Methanol → 7-[(Butan-2-yl)oxy]-5-methoxy-2,2-dimethyl-2H-1-benzopyran

HRID 1607654Notes

Reaction equation

HRID 1607654 reaction equation
CO.[CH3:3][O:4][C:5]1[CH:14]=[C:13]([O:15][CH:16]([CH2:18][CH3:19])[CH3:17])[CH:12]=[C:11]2[C:6]=1[C:7](=O)[CH2:8][C:9]([CH3:21])([CH3:20])[O:10]2.[BH4-].[Na+]>O1CCCC1>[CH3:3][O:4][C:5]1[CH:14]=[C:13]([O:15][CH:16]([CH2:18][CH3:19])[CH3:17])[CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([CH3:20])([CH3:21])[O:10]2

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 70381861HCID 70381861, compound

Product 1

HCID 1853307-[(Butan-2-yl)oxy]-5-methoxy-2,2-dimethyl-2H-1-benzopyranYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of 60 ml of tetrahydrofuran and 40 ml of methanol 5.6 g (20 millimoles) of 5-methoxy-7-sec. butoxy-2,2-dimethyl-4-chromanone are dissolved, whereupon 1.5 g (40 millimoles) of sodium tetrahydroborate are added in small portions and the reaction mixture is heated to boiling for 2 hours. The reaction mixture is worked up according to Example 31. The product is purified by column chromatography. Thus 4.4 g of the desired compound are obtained in the form of a light yellow oil, yield 85%.

Workup

  1. additionare added in small portions
  2. temperaturethe reaction mixture is heated
  3. customThe product is purified by column chromatography

Sources & evidence

ORD record
ord-89f3d7965cf04c1e9f546276cf827b07
Source dataset
uspto-grants-1989_09
Patent number
US04866089

Reaction notes

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