Sodium → HCID 15171888, compound

HRID 256861Notes

Reaction equation

HRID 256861 reaction equation
[OH:1][C:2]1[C:3]([CH3:28])=[C:4]([CH3:27])[C:5]2[O:10][C:9]([C:12]3[O:13][C:14]4[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH:23]=[O:24])=[CH:17][C:15]=4[CH:16]=3)([CH3:11])[CH2:8][CH2:7][C:6]=2[C:25]=1[CH3:26].[Na]>C(O)C>[OH:1][C:2]1[C:3]([CH3:28])=[C:4]([CH3:27])[C:5]2[O:10][C:9]([C:12]3[O:13][C:14]4[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH2:23][OH:24])=[CH:17][C:15]=4[CH:16]=3)([CH3:11])[CH2:8][CH2:7][C:6]=2[C:25]=1[CH3:26]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 15171886HCID 15171886, compound

Product 1

HCID 15171888HCID 15171888, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.2 g of rac-2-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)-7-methoxy-5-benzofurancarboxaldehyde and 20 mg of sodium borohyride in 5 ml of ethanol was stirred under nitrogen for 30 minutes. It was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over sodium sulfate and evaporated. Crystallization from ether/hexane yielded colorless crystals with m.p. 122°-125°.

Workup

  1. customIt was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customCrystallization from ether/hexane yielded colorless crystals with m.p. 122°-125°

Sources & evidence

ORD record
ord-cf0a428f074f48d7917e1532310533b8
Source dataset
uspto-grants-1993_11
Patent number
US05260294

Reaction notes

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