Water → HCID 86633442, compound

HRID 1881192Notes

Reaction equation

HRID 1881192 reaction equation
[CH2:1]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([OH:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].N12CCCN=C1CCCCC2.O>CN(C)C=O>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][O:19][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:16]([O:17][CH3:18])=[CH:15][C:12]=1[CH:13]=[O:14])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15947956HCID 15947956, compound

Product 1

HCID 86633442HCID 86633442, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Benzyloxy-2-hydroxy-5-methoxybenzaldehyde (2.9 g), ethyl bromoacetate (2.3 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.1 g) in N,N-dimethylformamide (30 ml) were heated at 100° C. under nitrogen for 5 hours. After cooling to room temperature, water was added and the mixture extracted with ethyl acetate. Ethyl acetate was washed with 1 N NaOH and 1 N HCl, dried with Na2SO4 and evaporated to dryness.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washEthyl acetate was washed with 1 N NaOH and 1 N HCl
  3. dry with materialdried with Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-0f7fa2acdaeb45d983b489bb2c2528f6
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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