Sulfuric Acid → HCID 66817332, compound

HRID 1755066Notes

Reaction equation

HRID 1755066 reaction equation
COCCO[AlH2-]OCCOC.[Na+].C([O:20][C:21]([CH:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH:30]=[C:31](F)[F:32])[CH2:25][CH2:24]1)=O)C1C=CC=CC=1.OS(O)(=O)=O>C1(C)C=CC=CC=1>[F:32]/[CH:31]=[CH:30]/[CH2:29][CH:26]1[CH2:27][CH2:28][CH:23]([CH2:21][OH:20])[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 16684438Red-AlHCID 66817873HCID 66817873, compound

Product 1

HCID 66817332HCID 66817332, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
85 °C

Procedure

A 3.3 M Red-Al solution in toluene (0.25 ml, 0.82 mmol) was added to a solution of 4-(3,3-difluoro-allyl)-cyclohexanecarboxylic acid benzyl ester (cis:trans=5.4:1) (42.8 mg, 0.145 mmol) in toluene (0.12 mL), and the mixture was stirred at 85° C. for 17 hours. The reaction mixture was poured into ice water, adjusted to pH 3 with a 4 N aqueous H2SO4 solution and extracted with ether. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give [4-((E)-3-fluoro-allyl)-cyclohexyl]-methanol (25.0 mg, 100%).

Workup

  1. extractionextracted with ether
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7eb056ea8312480880b6f11692b235b3
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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