Trichloroacetimidate as an efficient protective group for alcohols

Synlett

Volumn , Issue 6, 1999, Pages 753-755

  Yu, Biao ^a   Yu, Hai ^b   Hui, Yongzheng ^a   Han, Xiuwen ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Alcohol; Protective group; Trichloroacetimidate

Indexed keywords

ACETONITRILE DERIVATIVE; ALCOHOL DERIVATIVE; HYDROXYL GROUP; TRICHLOROACETIMIDIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032997491     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2736     Document Type: Article

References (30)

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25. 4Cl (27 mg, 1.0 mmol). After being refluxed for 5 min, the mixture was filtered. The filtrates were concentrated to a residue, which was purified by a silica gel column to give 1a (53 mg, 99%).
26. 3). 1b: 8.55 (1H, s), 5.92 (1H, d, J = 3.7), 5.32 (1H, d, J = 2.6), 4.62 (1H, d, J = 3.6), 4.38 (1H, t, J = 6.2), 4.30 (1H, dd, J = 7.5, 2.5), 4.13 (1H, t, J = 7.2), 4.02 (1H, m), 1.53, 1.41, 1.32, 1.29 (3H each, s each). 2b: 8.20 (1H, brs), 4.27 (2H, t, J = 6.5), 4.03 (2H, t, J = 6.8), 2.03 (3H, s), 1.78 (2H, m), 1.59 (2H, m), 1.43-1.25 (12H, m); 3b: 8.21 (1H, brs), 4.27 (2H, t, J = 6.5), 3.59 (2H, t, J = 6.5), 1.76 (2H, m), 1.51-1.28 (14H, m), 0.88 (9H, s), 0.03 (6H, s). 4b: 8.45 (1H, s), 8.02-7.80 (5H, m), 5.93 (1H, m), 5.60 (3H, m), 5.32 (2H, m), 4.88 (1H, s), 4.24 (1H, dd, J= 12.8, 5.1), 4.10 (2H, m), 2.14 (3H, s), 1.31 (3H, d, J = 6.3).
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29. 3) data for compounds 5-9. 5: 8.05 (2 H, m), 7.60 (1H, m), 7.46 (2H, m), 5.26 (1H, m), 5.16-5.09 (2H, m), 4.26 (2H, m), 3.23 (1 H, d, J = 4.1), 2.44 (1H, d, J = 9.7), 2.19 (3H, s), 1.28 (3H, d, J = 6.2); 6: 8.79 (1H, s), 8.57 (1H, s), 8.01 (2H, m), 7.60 (1H, m), 7.46 (2H, m), 6.47 (1H, d, J = 1.6), 5.69-5.57 (3H, m), 4.26 (1H, m), 1.89 (3H, s), 1.32 (3H, d, J = 6.3); 8: 8.02 (4H, m), 7.56 (2H, m), 7.43 (4H, m), 5.48-5.26 (5H, m), 5.12 (2H, m), 4.37 (1H, dd, J = 9.7, 3.4), 4.30 (1H, m), 4.12 (1H, m), 2.66 (2H, m), 2.29 (3H, s), 1.78 (3H, s), 1.27 (9H, m); 9: 8.04 (4H, m), 7.57 (2H, m), 7.47 (4H, m), 5.41 (2H, m), 5.27 (3H, m), 4.95 (1H, d, J = 1.5), 4.32 (2H, m), 4.04 (1H, m), 3.78 (1H, m), 2.63 (2H, m), 2.23 (3H, s), 1.89 (3H, s), 1.26 (9H, m).
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