Ethyl bromoacetate → HCID 54349507, compound

HRID 2050643Notes

Reaction equation

HRID 2050643 reaction equation
O=[C:2]([C:15]1[CH:16]=[C:17]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:18][CH:19]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(OC(=O)C)(=O)C>C1C=CC=CC=1.[Zn]>[CH2:3]([C:2]([C:15]1[CH:16]=[C:17]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:18][CH:19]=1)=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 7918Acetic AnhydrideHCID 15132295HCID 15132295, compound2×

Product 1

HCID 54349507HCID 54349507, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 4-(1-ketotridecyl)-2-trimethylsilylfuran (Compound 26, 84.5 mg, 0.25 mmol), zinc (100 mg, 1.53 mmol) and ethyl bromoacetate (105 mg, 0.63 mmol) in benzene (6 ml) was refluxed for 2 hours. After cooling to 0°, acetic anhydride (83 ul, 0.88 mmol) was added. Stirring was continued for 14 hours while the cooling bath attained room temperature. The mixture was washed with 5% sodium bicarbonate and water. Evaporation of the dried (magnesium sulfate) organic phase gave a residue which was purified by a silica column using 2% ethyl ether/hexane to give the title ester.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling to 0°
  3. washThe mixture was washed with 5% sodium bicarbonate and water
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate) organic phase
  6. customgave a residue which
  7. customwas purified by a silica column

Sources & evidence

ORD record
ord-13b0975b9c3b4cd2ad51ec7c7786714b
Source dataset
uspto-grants-1991_05
Patent number
US05013850

Reaction notes

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