Dimethylformamide → 4-Benzyloxy-3-cyclopentyloxybenzaldehyde

HRID 1819364Notes

Reaction equation

HRID 1819364 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[O:5][C:6]1[CH:11]=[C:10](OC)[CH:9]=[CH:8][C:7]=1[CH:14]1CN(C2C=C(C=CC=2)C(N)=O)C(=O)C1.[CH:32]1(Br)[CH2:36][CH2:35][CH2:34][CH2:33]1.[C:38]([O-])([O-])=[O:39].[K+].[K+].CN(C=[O:48])C>>[CH2:6]([O:5][C:4]1[CH:3]=[CH:2][C:31]([CH:38]=[O:39])=[CH:30][C:29]=1[O:48][CH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)[C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:14]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 57566938HCID 57566938, compound

Product 1

HCID 211878994-Benzyloxy-3-cyclopentyloxybenzaldehydeYield 98%

Procedure

To a solution of 4-benzyloxy-3-hydroxybenzaldehyde 13 (5 g, 21.9 mmol) in DMF (50 mL) was added cyclopentyl bromide (4.7 mL, 43.8 mmol) and K2CO3 (12.1 g, 87.6 mmol). The reaction mixture was stirred at r.t. overnight. K2CO3 was filtered from the mixture, and the filtrate was extracted with EtOAc. The organic layer was washed with water (2×) and saturated NaCl, dried with Na2SO4 and concentrated under reduced pressure. Purification by silica gel gave the desired product as a colorless oil (98%). Under high vacuum the oil solidified to a white solid.

Workup

  1. filtrationK2CO3 was filtered from the mixture
  2. extractionthe filtrate was extracted with EtOAc
  3. washThe organic layer was washed with water (2×) and saturated NaCl
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel

Sources & evidence

ORD record
ord-cd9172fd27f341a98ac2229a296fe902
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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