Sodium borohydride → 4-(5-Phenoxypent-1-ynyl)benzyl alcohol

HRID 2249033Notes

Reaction equation

HRID 2249033 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[O:1]([CH2:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][OH:18])=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 145767804-(5-Phenoxypent-1-ynyl)benzaldehyde

Product 1

HCID 145767814-(5-Phenoxypent-1-ynyl)benzyl alcoholYield 101.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.02 g of 4-(5-phenoxy-1-pentyn-1-yl)benzaldehyde in 5 ml of absolute ethanol was stirred with 0° C. bath cooling and 640 mg of sodium borohydride was added in portions. After stirring for 55 minutes the reaction mixture was quenched by the addition of water and then evaporated in vacuo. The residue was mixed cautiously with 2% sulfuric acid and extracted twice with ethyl acetate. The combined extracts were washed with saturated sodium chloride and then a sodium hydrogen carbonate solution. They were dried over magnesiumsulfate and evaporated in vacuo to yield 2.06 g of the 4-(Phenoxy-1-pentyn-1-yl)-benzyl alcohol which was sufficiently pure to use without purification.

Workup

  1. temperaturecooling
  2. customwas quenched by the addition of water
  3. customevaporated in vacuo
  4. additionThe residue was mixed cautiously with 2% sulfuric acid
  5. extractionextracted twice with ethyl acetate
  6. washThe combined extracts were washed with saturated sodium chloride
  7. dry with materialThey were dried over magnesiumsulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-85e440bc213248d590b99b14e97d223f
Source dataset
uspto-grants-1991_08
Patent number
US05041638

Reaction notes

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