Water → [2-(3-Fluoro-4-methoxy-phenyl)-cyclopropyl]-methanol

HRID 62897Notes

Reaction equation

HRID 62897 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([F:17])[CH:10]=1)=O)C.[Li+].[BH4-].O>C1COCC1>[F:17][C:11]1[CH:10]=[C:9]([CH:7]2[CH2:8][CH:6]2[CH2:4][OH:3])[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 58566289Ethyl 2-(3-fluoro-4-methoxyphenyl)cyclopropanecarboxylate

Product 1

HCID 22347600[2-(3-Fluoro-4-methoxy-phenyl)-cyclopropyl]-methanolYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

After 2-(3-fluoro-4-methoxy-phenyl)-cyclopropane carboxylic acid-ethyl ester (0.71 g, 2.98 mmol) was dissolved in anhydrous THF (10 mL), LiBH4-2.0M THF solution (3 mL, 5.96 mmol) was added thereto, and the mixture was stirred at 50° C. for 2 hours. After the termination of the reaction, the reactant was cooled to room temperature, added with water, and then extracted with EtOAc. The organic layer was separated, dried with MgSO4, and then concentrated under reduced pressure to obtain the title compound (0.519 g, 88%).

Workup

  1. customAfter the termination of the reaction
  2. temperaturethe reactant was cooled to room temperature
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-991dbf733fd44ddbb49ee99f0828f5f2
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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