Methanol → 6,6-Difluoro-5-methyl-5-hexenol

HRID 917400

Reaction equation

HRID 917400 reaction equation
O1CCCC1.[F:6][C:7]([F:17])=[C:8]([CH3:16])[CH2:9][CH2:10][CH2:11][C:12](OC)=[O:13].[BH4-].[Na+].CO>O>[F:6][C:7]([F:17])=[C:8]([CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 23020142Methyl 6,6-difluoro-5-methyl-5-hexenoate

Product 1

HCID 230201726,6-Difluoro-5-methyl-5-hexenolYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 110 ml of tetrahydrofuran, 53 g (0.30 mol) of methyl 6,6-difluoro-5-methyl-5-hexenoate was dissolved, followed by adding 23 g (0.61 mmol) of sodium borohydride, heating the mixture under refluxing and slowly drop-wisely adding 50 ml of methanol. After the end of the drop-wise addition, the reaction liquid was stirred under refluxing for 1 hour, followed by cooling to room temperature, adding water and extracting with diethyl ether. The organic layer was washed with water, dilute hydrochloric acid and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate, and concentrating under reduced pressure to obtain 36.5 g (yield: 82%) of 6,6-difluoro-5-methyl-5-hexenol.

Workup

  1. temperatureheating the mixture
  2. temperatureunder refluxing
  3. additionAfter the end of the drop-wise addition
  4. customthe reaction liquid
  5. temperatureunder refluxing for 1 hour
  6. extractionextracting with diethyl ether
  7. washThe organic layer was washed with water, dilute hydrochloric acid
  8. dry with materialby drying over anhydrous magnesium sulfate
  9. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-f94103283e3a493f90b1121e614493ee
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Linked notes

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