Ethyl bromoacetate → HCID 54185006, compound

HRID 1579105Notes

Reaction equation

HRID 1579105 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]([CH:17]1[C:25]2[C:20](=[CH:21][C:22]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:23][CH:24]=2)[CH2:19][CH2:18]1)=[O:16].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>O1CCCC1>[CH2:37]([O:36][C:34](=[O:35])[CH2:33][C:17]1([C:15]([O:14][CH3:13])=[O:16])[C:25]2[C:20](=[CH:21][C:22]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:23][CH:24]=2)[CH2:19][CH2:18]1)[CH3:38]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 7912DiisopropylamineHCID 119850Methyl 5-cyclohexyl-2,3-dihydro-1H-indene-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 54185006HCID 54185006, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-20 °C

Procedure

23.6 ml of butyl-lithium (20% strength in hexane) are slowly added dropwise to a solution of 7.6 g of diisopropylamine (absolute) in 80 ml of absolute tetrahydrofurane at -10° to -15°C under a dry nitrogen atmosphere, whilst stirring, and 15 minutes after completion of the addition a solution of 15.5 g of 5-cyclohexyl-1-indanecarboxylic acid methyl ester in 40 ml of absolute tetrahydrofurane is added. The reaction solution is cooled to -20°C and a solution of 16.5 g of ethyl bromoacetate in 40 ml of absolute tetrahydrofurane is rapidly added dropwise. In the course thereof, the temperature rises to 0°C. The reaction solution is partitioned between three times 200 ml of methylene chloride and three times 200 ml of 2 N hydrochloric acid. The combined organic phases are washed with water, dried over sodium sulphate and evaporated in vacuo. Distillation of the evaporation residue in a high vacuum yields 1-methoxycarbonyl-5-cyclohexyl-1-indaneacetic acid ethyl ester in the fraction boiling at 140°-142°C/0.04 mm Hg.

Workup

  1. additionis added
  2. customrises to 0°C
  3. customThe reaction solution is partitioned between three times 200 ml of methylene chloride and three times 200 ml of 2 N hydrochloric acid
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. distillationDistillation of the evaporation residue in a high vacuum

Sources & evidence

ORD record
ord-eebe7dc609f549269d46194490e4f99c
Source dataset
uspto-grants-1976_02
Patent number
US03940434

Reaction notes

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