Sodium hydride → 4-Cyclopropylmethoxy-2,6-difluoro-benzylalcohol

HRID 1794141Notes

Reaction equation

HRID 1794141 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[C:8]([F:12])[C:9]=1[CH2:10][OH:11].[CH:14]1([CH2:17]Br)[CH2:16][CH2:15]1>CN(C)C=O>[CH:14]1([CH2:17][O:13][C:6]2[CH:5]=[C:4]([F:3])[C:9]([CH2:10][OH:11])=[C:8]([F:12])[CH:7]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 222199753,5-Difluoro-4-(hydroxymethyl)phenol

Product 1

HCID 222200444-Cyclopropylmethoxy-2,6-difluoro-benzylalcoholYield 134%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (82 mg, 55%, 1.87 mM) was added to a solution of 3,5-difluoro-4-hydroxymethyl-phenol (300 mg, 1.87 mM) in dimethylformamide (4 mL). After 1 h stirring at room temperature cyclopropylmethylbromide (135 mg, 1.87 mM) was added and stirring continued for 24 h. The mixture was partitioned between water and diethylether. Organic phases were pooled, washed with brine and dried with MgSO4 to yield after evaporation a yellow oil (673 mg). This residue was purified by column chromatography (silica gel; n-hexane/ethylacetate gradient) to yield 287 mg (71%) of the product as a yellowish oil. MS (EI): 214.1 (M)+.

Workup

  1. additionwas added
  2. customThe mixture was partitioned between water and diethylether
  3. washwashed with brine
  4. dry with materialdried with MgSO4
  5. customto yield
  6. customafter evaporation a yellow oil (673 mg)
  7. customThis residue was purified by column chromatography (silica gel; n-hexane/ethylacetate gradient)

Sources & evidence

ORD record
ord-002d5b02980c4fe8be9b97e99a3f7393
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

Loading…