1-Phenyl-1,2-ethanediol → 2-(Tert-butyldimethylsilyl)oxy-1-phenylethanol

HRID 870470Notes

Reaction equation

HRID 870470 reaction equation
[C:1]1([CH:7]([OH:10])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][C:12]([Si:15](Cl)([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(N(CC)CC)C>O1CCCC1.O>[Si:15]([O:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:10])([C:12]([CH3:14])([CH3:13])[CH3:11])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 71491-Phenyl-1,2-ethanediolHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 113911162-(Tert-butyldimethylsilyl)oxy-1-phenylethanolYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a 250-mL 3-necked round-bottom flask was placed a solution of 1-phenylethane-1,2-diol (10 g, 72.38 mmol, 1.00 equiv), TBSCl (22 g, 145.97 mmol, 2.00 equiv) and triethylamine (14.7 g, 145.27 mmol, 2.00 equiv) in tetrahydrofuran (100 mL). The solution was stirred overnight at room temperature. The next day it was diluted with 150 mL of H2O and the mixture was extracted with 3×80 mL of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/10). Purification afforded 17 g (93%) of 2-[(tert-butyldimethylsilyl)oxy]-1-phenylethan-1-ol as a white oil.

Workup

  1. customInto a 250-mL 3-necked round-bottom flask was placed
  2. extractionthe mixture was extracted with 3×80 mL of ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customPurification

Sources & evidence

ORD record
ord-f681ec6dd6364511a42e9525608426e7
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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