Water → 5-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,3-dimethyl-pentan-1-ol

HRID 1806998Notes

Reaction equation

HRID 1806998 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:6][CH2:7][OH:8])[CH2:3][CH2:4][OH:5].[H-].[Na+].Br[CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].O>CN(C)C=O>[C:19]([Si:16]([CH3:18])([CH3:17])[O:15][CH2:14][CH2:13][O:5][CH2:4][CH2:3][C:2]([CH3:9])([CH3:1])[CH2:6][CH2:7][OH:8])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 128107743,3-Dimethylpentane-1,5-diol

Product 1

HCID 866404195-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,3-dimethyl-pentan-1-olYield 9.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step A To the solution of 3,3-dimethyl-pentane-1,5-diol (1.5 g, 11 mmol) prepared in Example 116a Step A. in anhydrous dimethylformamide (15 mL) was added NaH (60%, 0.68 g, 17 mmol). The mixture was stirred at room temperature for 15 min, then (2-bromoethoxy)-tert-butyldimethylsilane (3.3 g, 14 mmol) was added. The mixture was stirred at room temperature for 1 h. Water was added. The mixture was extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:3) to give 5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,3-dimethyl-pentan-1-ol as a yellow oil (0.3 g, 9%).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. extractionThe mixture was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc:hexanes=1:3)

Sources & evidence

ORD record
ord-b9aa0463f9cc443dbb855f4fdacdd276
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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