1,3-Propanediol → 3-(Tert-butyldiphenylsiloxy)propanol

HRID 222564Notes

Reaction equation

HRID 222564 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].C(N(C(C)C)CC)(C)C.[Si:15](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[Si:15]([O:4][CH2:3][CH2:2][CH2:1][OH:5])([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 81531DiisopropylethylamineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 102451343-(Tert-butyldiphenylsiloxy)propanolYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,3-propanediol (4.22 g, 55 mmol) in anhydrous CH2Cl2 (10 mL) under argon was treated with diisopropylethyl amine (10 mL) and tert-butyldiphenylsilyl chloride (5.00 mL, 5.29 g, 19.23 mmol). Stirring was continued for 2 h. The sample was concentrated, and the residue was purified by column chromatography (silica, hexanes/ethyl acetate (10:1)] affording a colorless oil (4.74 g, 78%): 1H NMR δ 1.07 (s, 9H), 1.78-1.86 (m, 2H), 2.46-2.50 (m, 1H), 3.83-3.88 (m, 4H), 7.37-7.48 (m, 6H), 7.68-7.75 (m, 4H); 13C NMR δ 19.33, 27.08, 34.52, 62.11, 63.46, 128.01, 130.03, 133.50, 135.80; FAB-MS obsd 315.1779, calcd 315.1780 [(M+H)+, M=C19H26O2Si].

Workup

  1. concentrationThe sample was concentrated
  2. customthe residue was purified by column chromatography (silica, hexanes/ethyl acetate (10:1)]

Sources & evidence

ORD record
ord-3fd19cef287a48d795e963860e9b2686
Source dataset
uspto-grants-2012_06
Patent number
US08207329B2

Reaction notes

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