Ethyl-4,4-difluorocyclohexane carboxylate → (4,4-Difluorocyclohexyl)methanol

HRID 1430230Notes

Reaction equation

HRID 1430230 reaction equation
[F:1][C:2]1([F:13])[CH2:7][CH2:6][CH:5]([C:8](OCC)=[O:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[F:1][C:2]1([F:13])[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 2779138Ethyl-4,4-difluorocyclohexane carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 21184133(4,4-Difluorocyclohexyl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl 4,4-difluorocyclohexanecarboxylate (1.000 g) in diethyl ether (5 mL) was added lithium aluminum hydride (1.0M in tetrahydrofuran) (6.24 mL) at 0° C. The reaction was allowed to warm to room temperature and was stirred for 2 hours. The reaction was cooled to 0° C. and quenched with water (0.24 mL). 15% Aqueous NaOH (0.24 mL) was added followed by more water (0.72 mL). The reaction was stirred for 1 hour, and magnesium sulfate was added. The mixture was filtered and concentrated to provide the title compound.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with water (0.24 mL)
  3. addition15% Aqueous NaOH (0.24 mL) was added
  4. stirringThe reaction was stirred for 1 hour
  5. additionmagnesium sulfate was added
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-242483f805d64008be4b75e8deb69f36
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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