Cyclohexanecarboxaldehyde → HCID 54379492, compound

HRID 1533267Notes

Reaction equation

HRID 1533267 reaction equation
C(N(C(C)C)CC)(C)C.C([Li])CCC.[CH2:15]1[O:23][C:22]2[CH:21]=[CH:20][C:19]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:18][C:17]=2[O:16]1.[CH:30]1([CH:36]=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>O1CCCC1.CCCCCC>[CH2:15]1[O:23][C:22]2[CH:21]=[CH:20][C:19]([CH:24]([CH:36]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[OH:37])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:18][C:17]=2[O:16]1

Participants

7

Reactant 4

HCID 16275CyclohexanecarboxaldehydeHCID 81531DiisopropylethylamineHCID 5845741,3-Benzodioxole-5-acetic acid, ethyl esterHCID 178418339Butyllithium

Product 1

HCID 54379492HCID 54379492, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of N,N-diisopropyl-N-ethylamine (4.49 g) in tetrahydrofuran (50 ml) was added with stirring 1.6M n-butyl lithium in n-hexane solution (27.6 ml) below 0° C. under a nitrogen atmosphere. After the mixture was stirred in an ice-bath for 30 minutes, a solution of ethyl 3,4-methylenedioxyphenylacetate (3.85 g) in tetrahydrofuran (40 ml) was added at −78° C. The mixture was stirred for 30 minutes and cyclohexanecarbaldehyde (2.49 g) was added. After being stirred for 15 minutes at the same temperature, the mixture was quenched by saturated aqueous ammonium acetate. The mixture was extracted with diethyl ether (100 ml), and the solution was washed with 1M hydrochloric acid and brine successively, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=6:1) to give ethyl (2RS,3RS)-2-(3,4-methylenedioxyphenyl)-3-cyclohexyl-3-hydroxypropionate (4.45 g) as an oil.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. stirringAfter being stirred for 15 minutes at the same temperature
  3. customthe mixture was quenched by saturated aqueous ammonium acetate
  4. extractionThe mixture was extracted with diethyl ether (100 ml)
  5. washthe solution was washed with 1M hydrochloric acid and brine successively
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-89ca6446553a4bc08e2e2a839a968bae
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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