Nitrogen → 1-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-

HRID 2218445Notes

Reaction equation

HRID 2218445 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].C(N(C(C)C)CC)(C)C.[C:16]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])([CH3:18])[CH3:17].N#N>ClCCl>[C:16]([Si:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 947NitrogenHCID 80641,4-ButanediolHCID 81531DiisopropylethylamineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 100651081-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-Yield 172.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4-butanediol (5 g, 55 mol) in dichlormethane (10 mL) containing diisopropylethylamine (10 mL) was added tert-butylchlorodiphenylsilane (5 mL, 18 mmol) dropwise under N2 atmosphere at 18° C. over 2 h. The resultant solution was stirred at room temperature for 4 hours and concentrated under reduced pressure. Purification by column chromatography with hexane/ethyl acetate (1/1) gave 4-(tert-butyl-diphenyl-silanyloxy)-butan-1-ol (10.2 g, 85% yield) as colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.62-7.71 (4H, m); 7.32-7.43 (6H, m), 3.63-3.69 (4H, m), 1.83 (1H, br s), 1.59-1.71 (4H, m), 1.03 (9H, s).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification by column chromatography with hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-7c62505766414c36a7f98c5f8d1f1a2f
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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