Benzyl Bromide → HCID 12085336, compound

HRID 896445Notes

Reaction equation

HRID 896445 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:11]2)=[CH:6][C:5]=1[O:19][CH3:20].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH2:21]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:11]2)=[CH:6][C:5]=1[O:19][CH3:20])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 12085335HCID 12085335, compound

Product 1

HCID 12085336HCID 12085336, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 8.9 mmol of a 60% strength suspension of sodium hydride in paraffin oil are added a little at a time to 1.86 g of ethyl 7-hydroxy-6-methoxy-2-chromancarboxylate in 23 ml of dimethylformamide. The mixture is stirred at room temperature for 60 minutes, and 8.1 mmol of benzyl bromide are then added. The reaction mixture is stirred at room temperature for 5 hours. For aqueous work-up (three times washing with water, once with saturated sodium chloride solution), the mixture is diluted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated. Two recrystallizations from cyclohexane give pure ethyl 7-(benzyloxy)-6-methoxy-2-chromancarboxylate; further product fractions are obtained from the mother liquors of the recrystallizations by preparative HPLC purification (column; chromsil, mobile phase: acetonitrile/water).

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 5 hours
  2. washFor aqueous work-up (three times washing with water, once with saturated sodium chloride solution), the mixture
  3. additionis diluted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated
  6. customTwo recrystallizations from cyclohexane

Sources & evidence

ORD record
ord-cd319fa815464179af565d9badd364e4
Source dataset
uspto-grants-2005_07
Patent number
US06919360B2

Reaction notes

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