Methyl Acrylate → (S)-1-Ethyl-2-oxocyclohexanepropanoic Acid Methyl Ester

HRID 247647Notes

Reaction equation

HRID 247647 reaction equation
C[C@H](C1C=CC=CC=1)N=[C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[CH2:10][CH3:11].[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].[O:24]1CCCC1>>[CH3:23][O:22][C:18](=[O:21])[CH2:19][CH2:20][C@:5]1([CH2:10][CH3:11])[CH2:6][CH2:7][CH2:8][CH2:9][C:4]1=[O:24]

Participants

4

Reactant 3

HCID 7294Methyl AcrylateHCID 8028TetrahydrofuranHCID 10398941(R)-alpha-Methyl-N-(2-ethylcyclohexylidene)-benzenemethanamine

Product 1

HCID 10375892(S)-1-Ethyl-2-oxocyclohexanepropanoic Acid Methyl EsterYield 57%

Procedure

A solution of (R)-α-methyl-N-(2-ethylcyclohexylidene)-benzenemethanamine (1.303 kg, 5.68 mol), and methyl acrylate (5.68 mol, 489 g, 511 mL) in 2.5 L of dry tetrahydrofuran was sealed under nitrogen and placed in the dark for 21 days. The tetrahydrofuran was then removed on a rotary evaporator and the residue was divided in half. Each half was stirred for 1.5 hours in 3.5 L of 1M hydrochloric acid and extracted with ether (4×700 mL). The extracts were combined, washed with 1M hydrochloric acid (2×500 mL), 1M sodium hydroxide (500 mL) and brine (500 mL). The two halves were combined and concentrated affording 689 g (3.25 mol, 57%) of yellow oil.

Workup

  1. customThe tetrahydrofuran was then removed on a rotary evaporator
  2. extractionextracted with ether (4×700 mL)
  3. washwashed with 1M hydrochloric acid (2×500 mL), 1M sodium hydroxide (500 mL) and brine (500 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-00e821a282f446acab5e4b16103cc5d9
Source dataset
uspto-grants-1987_11
Patent number
US04709048

Reaction notes

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