Water → HCID 10157910, compound

HRID 842105Notes

Reaction equation

HRID 842105 reaction equation
[BH4-].[Na+].[CH:3]1([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[CH2:12][C:13]2[O:14][C:15]3[C:21]([CH2:22][CH:23]=[O:24])=[CH:20][C:19]([Cl:25])=[CH:18][C:16]=3[N:17]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.O>C(O)C>[CH:3]1([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[CH2:12][C:13]2[O:14][C:15]3[C:21]([CH2:22][CH2:23][OH:24])=[CH:20][C:19]([Cl:25])=[CH:18][C:16]=3[N:17]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10200962HCID 10200962, compound

Product 1

HCID 10157910HCID 10157910, compoundYield 109.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride 0.05 g, 0.0013 mol) was added to a stirred solution of 2-(3-cyclopentyloxy-4-methoxybenzyl)-5-chlorobenzoxazole-7-ethanal (1.0 g, 0.0025 mol) in 10 ml ethanol. Stirring was continued for 1 hour. Water (15 ml) was added and the reaction mixture was extracted with 2×50 ml ethyl acetate. The ethyl acetate layer was washed once with water (50 ml), dried and evaporated to give 1.1 g of pale yellow crystals. A small sample of this solid was recrystallized from a blend of ether-hexane to give the title compound as a white solid, mp 74-76° C.

Workup

  1. extractionthe reaction mixture was extracted with 2×50 ml ethyl acetate
  2. washThe ethyl acetate layer was washed once with water (50 ml)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-1428e612bde342c391c0ddca8e3ce286
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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