Dimethylformamide → 6-Benzyloxy-2-(dimethoxymethyl)-2,5,7,8-tetramethyl-chroman

HRID 462586Notes

Reaction equation

HRID 462586 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[C:4]1([CH3:18])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([CH3:17])[C:8]([CH3:16])=[C:9]([OH:15])[C:10]=2[CH3:14])[O:5]1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].CN(C)C=O>O>[CH2:21]([O:15][C:9]1[C:10]([CH3:14])=[C:11]2[C:6](=[C:7]([CH3:17])[C:8]=1[CH3:16])[O:5][C:4]([CH:3]([O:2][CH3:1])[O:19][CH3:20])([CH3:18])[CH2:13][CH2:12]2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 130515422-(Dimethoxymethyl)-6-hydroxy-2,5,7,8-tetramethyl-chroman

Product 1

HCID 130515436-Benzyloxy-2-(dimethoxymethyl)-2,5,7,8-tetramethyl-chroman

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.47 g (5.25 mmoles) of the chroman obtained in Example 8 were heated at 100° C. with 3.2 g of benzyl bromide, 1.5 g of Na2CO3 and 7 ml of dimethylformamide for 13 hours, and water was then added. This mixture was extracted with heptane, after which the crude product obtained from the extract phase was chromatographed on 50 g of silica gel using a mixture of 1 part by volume of ether and 2 parts by volume of heptane. The following fractions were obtained: F1=1.28 g; F2 (mixed fraction)=0.13 g; F3 (starting material)=0.23 g.

Workup

  1. extractionThis mixture was extracted with heptane

Sources & evidence

ORD record
ord-2794d63136934f48b433fcb63b2bc159
Source dataset
uspto-grants-1985_05
Patent number
US04515975

Reaction notes

Loading…