Dimethylformamide → HCID 67287398, compound

HRID 74986Notes

Reaction equation

HRID 74986 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([O:15][CH3:16])[CH:10]1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].CN(C=O)C.N1C=NCC=1>CN(C)C1C=CN=CC=1.CCOCC>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([O:15][CH3:16])[CH:10]1[O:17][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 127446564H-ImidazoleHCID 151872871-Benzyloxy-3-methoxy-cyclohexan-2-ol2×

Product 1

HCID 67287398HCID 67287398, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-benzyloxy-3-methoxy-cyclohexan-2-ol, 51d, (2.31 g, 9.78 mmol), tert-butyl-chlorodimethyl-silane (2.21 g, 2.73 mL, 14.66 mmol) in 20 dry DMF at room temperature was added 4H-imidazole (1.997 g, 29.33 mmol) and a catalytic amount of 4-dimethylaminopyridine (0.12 g, 0.98 mmol). The resulting mixture was stirred at room temperature overnight. It was then diluted with ether, washed with water, aqueous saturated citric acid solution and water again. The organic phase was dried with MgSO4, filtered and concentrated in vacuo. The colorless crude oil was used directly in the next step without further purification.

Workup

  1. washwashed with water, aqueous saturated citric acid solution and water again
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe colorless crude oil was used directly in the next step without further purification

Sources & evidence

ORD record
ord-3ffd812bbcf141c3bf50331d958cc488
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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