Benzyl Bromide → HCID 13091191, compound

HRID 1902659Notes

Reaction equation

HRID 1902659 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:20])[CH:11]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[CH2:27]([O:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:20])[CH:11]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13091187HCID 13091187, compound

Product 1

HCID 13091191HCID 13091191, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 5-(3,4-dihydroxyphenyl)-4-oxo-4H-pyran-2-carboxylate (3.0 g), anhydrous potassium carbonate (6.0 g) and benzyl bromide (3.0 ml) in dry DMF (30 ml) was stirred at room temperature for 2 hours and then filtered. The filtrate was cooled, acidified with 2 N hydrochloric acid (20 ml) and diluted with water (80 ml). The solid product was recrystallised from ethanol to give ethyl 5-(3,4-dibenzyloxyphenyl)-4-oxo-4H-pyran-2-carboxylate (mp 122°-125° C.).

Workup

  1. filtrationfiltered
  2. temperatureThe filtrate was cooled
  3. additiondiluted with water (80 ml)
  4. customThe solid product was recrystallised from ethanol

Sources & evidence

ORD record
ord-456bf420db59460d96862d855b0a45ed
Source dataset
uspto-grants-1982_12
Patent number
US04364956

Reaction notes

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