Sodium borohydride → HCID 66674526, compound

HRID 424029Notes

Reaction equation

HRID 424029 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:23](=[O:39])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:27][CH:26]=2)[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C1COCC1>[CH2:16]([O:15][C:13]1[CH:12]=[C:11]([CH:23]([OH:39])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[CH:29][CH:30]=2)[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 66673645HCID 66673645, compound

Product 1

HCID 66674526HCID 66674526, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2 g (3.9 mmol) of recrystallized 1-(3,5-dibenzyloxyphenyl)-2-(4-benzyloxyphenyl)ethanone prepared according to Example 5 are introduced into a 100 ml round-bottomed flask and are dissolved in 30 ml of methanol and 25 ml of THF. Approximately 0.147 g of sodium borohydride is added in small fractions at ambient temperature over 1 hour. The medium is kept stirred for 1 h and concentrated, 30 ml of water are added and the medium is extracted with 60 ml of MTBE. The MTBE phase is concentrated to produce 2 g of a light yellow oil which crystallizes over time. 5 ml of methanol are added to this product, the mixture is kept stirred for 1 h and then the white precipitate obtained is filtered off. After drying at vacuum at 35° C., 1.3 g of 1-(3,5-dibenzyloxyphenyl)-2-(4-benzyloxyphenyl)ethanol are recovered in the form of a white solid with a melting point of 80-81° C., i.e. a yield of 65% with respect to the starting ketone.

Workup

  1. additionare introduced into a 100 ml round-bottomed flask
  2. concentrationconcentrated
  3. addition30 ml of water are added
  4. extractionthe medium is extracted with 60 ml of MTBE
  5. concentrationThe MTBE phase is concentrated

Sources & evidence

ORD record
ord-a02233e42027496383fcab62d3f19a91
Source dataset
uspto-grants-2012_01
Patent number
US08101804B2

Reaction notes

Loading…