Ethyl bromoacetate → HCID 10280958, compound

HRID 1351037Notes

Reaction equation

HRID 1351037 reaction equation
[F:1][C:2]([F:33])([F:32])[CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31].[H-].[Na+].Br[CH2:37][C:38]([O:40]CC)=[O:39].[OH-].[Na+]>O1CCCC1.C(O)C>[F:1][C:2]([F:32])([F:33])[CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:37][C:38]([OH:40])=[O:39]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 21097608HCID 21097608, compound

Product 1

HCID 10280958HCID 10280958, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of the product of step (c) (750 mg) in tetrahydrofuran (15 mL) was added sodium hydride (60% dispersion in mineral oil, 91 mg). The reaction was stirred at 20° C. for 30 minutes then ethyl bromoacetate (335 μl) was added and the reaction was stirred for a further 15 hours. Ethanol (1 mL) was then added and the stirring continued for 5 minutes. Sodium hydroxide solution (2M, 10 mL) was added and the resulting mixture was stirred at 20° C. for 30 minutes. The reaction mixture was then partitioned between dichloromethane (40 mL) and water (40 mL). The aqueous layer was acidified to pH 1 by the addition of hydrochloric acid (2M) and then extracted with dichloromethane (2×40 mL). The combined organic layers were dried and the solvent removed in vacuo to give the title compound as a yellow oil (612 mg).

Workup

  1. stirringthe reaction was stirred for a further 15 hours
  2. waitthe stirring continued for 5 minutes
  3. stirringthe resulting mixture was stirred at 20° C. for 30 minutes
  4. customThe reaction mixture was then partitioned between dichloromethane (40 mL) and water (40 mL)
  5. additionThe aqueous layer was acidified to pH 1 by the addition of hydrochloric acid (2M)
  6. extractionextracted with dichloromethane (2×40 mL)
  7. customThe combined organic layers were dried
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0bf1546959244942b7b4cb6a1728c244
Source dataset
uspto-grants-2007_05
Patent number
US07217409B2

Reaction notes

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