Sodium borohydride → (6-Fluoro-3-pentylchroman-7-yl)methanol

HRID 2420647Notes

Reaction equation

HRID 2420647 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12]=[O:13])[O:8][CH2:7][CH:6]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:5]2.[BH4-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][OH:13])[O:8][CH2:7][CH:6]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:5]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 592883516-Fluoro-3-pentylchroman-7-carbaldehyde

Product 1

HCID 59288346(6-Fluoro-3-pentylchroman-7-yl)methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

11.1 g (44.3 mmol) of 6-fluoro-3-pentylchroman-7-carbaldehyde are dissolved in 100 ml of ethanol, and 2.0 g (52.8 mmol) of sodium borohydride are added in portions. After 3 h, the batch is diluted with water and extracted three times with MTB ether. The combined org. phases are washed with sat. sodium chloride soln. and dried over sodium sulfate, the solvent is removed in vacuo, and the residue is filtered through silica gel with dichloromethane (Rf=0.3), giving (6-fluoro-3-pentylchroman-7-yl)methanol as a colourless solid.

Workup

  1. extractionextracted three times with MTB ether
  2. washphases are washed with sat. sodium chloride soln
  3. dry with materialand dried over sodium sulfate
  4. customthe solvent is removed in vacuo
  5. filtrationthe residue is filtered through silica gel with dichloromethane (Rf=0.3)

Sources & evidence

ORD record
ord-576e7ebc033046578a1287017d8be0aa
Source dataset
uspto-grants-2011_06
Patent number
US07955664B2

Reaction notes

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