Tetrahydrofuran → Ethoxyprecocene

HRID 1607653Notes

Reaction equation

HRID 1607653 reaction equation
O1CCC[CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[O:20][C:19]([CH3:27])([CH3:26])[CH2:18][C:17]2=O>>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH2:25][CH3:2])[O:20][C:19]([CH3:27])([CH3:26])[CH:18]=[CH:17]2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 1033734H-1-Benzopyran-4-one, 2,3-dihydro-6,7-dimethoxy-2,2-dimethyl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 127846EthoxyprecoceneYield 88%

Procedure

In 80 ml of anhydrous tetrahydrofurane 5.0 g (20 millimoles) of 6-methoxy-7-methoxy-2,2-dimethyl-4-chromanone are dissolved whereupon 1.5 g of lithium aluminum hydride are added in small portions under stirring and the reaction mixture is heated to boiling for an hour. The reaction mixture is worked up according to Example 31. The product is purified by column chromatography. Thus 4.1 g of the desired compound are obtained in the form of a colorless oil, yield 88%.

Workup

  1. additionare added in small portions
  2. temperaturethe reaction mixture is heated
  3. waitto boiling for an hour
  4. customThe product is purified by column chromatography

Sources & evidence

ORD record
ord-9a53fcbe4a39471b82e18eec502761f5
Source dataset
uspto-grants-1989_09
Patent number
US04866089

Reaction notes

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