2,6-Lutidine → HCID 21638266, compound

HRID 1757698Notes

Reaction equation

[C:1]([O:7][CH2:8][C@H:9]([CH3:31])[CH2:10][C@H:11]([O:29][CH3:30])[C@@H:12]([OH:28])[C@@H:13]([O:26][CH3:27])[CH2:14][C@@H:15]([CH3:25])[CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].N1C(C)=CC=CC=1C.O([Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])S(C(F)(F)F)(=O)=O>C(=O)(O)[O-].[Na+]>[C:1]([O:7][CH2:8][C@H:9]([CH3:31])[CH2:10][C@H:11]([O:29][CH3:30])[C@@H:12]([O:28][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])[C@@H:13]([O:26][CH3:27])[CH2:14][C@@H:15]([CH3:25])[CH2:16][O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:19])[CH3:20])(=[O:6])[C:2]([CH3:5])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 25 °C

Procedure

Alcohol 24 (2.98 g, 6.48 mmol) was dissolved in 50 ml of methylene chlorideat 25° C. and 2,6-lutidine (1.51 ml, 2.0 equiv) was added. t-Butyldimethylsilyl triflate (2.23 ml, 1.5 equiv) was added and the mixture was stirred at 25° C. for 10-15 min. The solution was poured in 40 ml of saturated aqueous sodium bicarbonate solution and extracted with 2×200 ml of methylene chloride. The combined organic phases were dried over magnesium sulfate and concentrated in vacuo to give4.0 g of the bis-t-butyldimethylsilyl ether 25 as an oil. This material washomogeneous by 1H and 13C NMR and was used directly in the subsequent transformation.

Workup

extractionextracted with 2×200 ml of methylene chloride
dry with materialThe combined organic phases were dried over magnesium sulfate
concentrationconcentrated in vacuo to give4

Sources & evidence

ORD record: ord-2b411341f90e4c719431d43c43264743
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05446158

Reaction notes

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