Imidazole → HCID 59543150, compound

HRID 1970985Notes

Reaction equation

HRID 1970985 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([OH:15])[CH:11]([F:16])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][Si:21]([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22])[CH:11]([F:16])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 595431264-(Benzyloxy)-2-fluorocyclohexanol

Product 1

HCID 59543150HCID 59543150, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(benzyloxy)-2-fluorocyclohexanol (3.9 g, 17.4 mmol) in DMF (50 mL) were added TBSCl (3.93 g, 26.1 mmol) and imidazole (1.78 g, 26.1 mmol). The reaction was monitored by TLC. After completion of the reaction, the mixture was treated with sodium bicarbonate solution, and extracted with EtOAc. The combined organics were dried, concentrated, and purified by flash chromatography to afford the title compound.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with EtOAc
  3. customThe combined organics were dried
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-ad3f299e74ea40848ffa7c8067a2e45c
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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