Sodium borohydride → HCID 18793515, compound

HRID 1004760Notes

Reaction equation

HRID 1004760 reaction equation
[BH4-].[Na+].[F:3][CH:4]([F:20])[O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[O:14][CH:15]1[CH2:19][CH2:18][O:17][CH2:16]1>CO>[F:20][CH:4]([F:3])[O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][C:7]=1[O:14][CH:15]1[CH2:19][CH2:18][O:17][CH2:16]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18793514HCID 18793514, compound

Product 1

HCID 18793515HCID 18793515, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sodium borohydride solution (0.0177 mol) was added portionwise to a solution of intermediate 1 (0.0532 mol) in methanol (100 ml), and the reaction mixture was stirred for 1 hour at RT. The solvent was evaporated, the residue was washed with water, and extracted with CH2Cl2. The separated organic layer was dried, filtered, and the solvent was evaporated. The residue was purified by open column chromatography over silica gel (eluent: CH2Cl2 /2-propanone 96/4 and 90/10; CH2Cl2 /CH3OH 96/4). The pure fractions were collected and the solvent was evaporated, yielding 11.3 g (81%) of (±)-4-(difluoromethoxy)-3-[(tetrahydro-3-furanyl)oxy]benzenemethanol (intermediate 2).

Workup

  1. customThe solvent was evaporated
  2. washthe residue was washed with water
  3. extractionextracted with CH2Cl2
  4. customThe separated organic layer was dried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by open column chromatography over silica gel (eluent: CH2Cl2 /2-propanone 96/4 and 90/10; CH2Cl2 /CH3OH 96/4)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-dc93285e13fa4eca8e1a98ae13281d31
Source dataset
uspto-grants-2000_04
Patent number
US06051718

Reaction notes

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