Triethylamine → t-Butylpent-4-ynyloxy diphenyl silane

HRID 30585Notes

Reaction equation

HRID 30585 reaction equation
[C:1]([OH:6])#[C:2][CH2:3][CH2:4][CH3:5].[Si:7](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCN(CC)CC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:20]([Si:7]([O:6][CH2:1][CH2:2][CH2:3][C:4]#[CH:5])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 94078tert-ButyldiphenylchlorosilaneHCID 10866258Pentynol

Product 1

HCID 5461495t-Butylpent-4-ynyloxy diphenyl silaneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of pentynol (8.0 g, 95 mmol), t-butyldiphenylsilylchloride (28 g, 114 mmol) and Et3N (14 g, 138 mmol) in CH2Cl2 is stirred at room temperature for 16 h, treated with 1M K2CO3 and extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated in vacuo. The residue is purified by filtration on a silica pad to obtain 30 g of t-butylpent-4-ynyloxy diphenyl silane (yield: 98%

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined extracts are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. filtrationThe residue is purified by filtration on a silica pad

Sources & evidence

ORD record
ord-a4503c5eb7224d55b81763f390f48172
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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