Hydrochloric Acid → HCID 54110933, compound

HRID 378216Notes

Reaction equation

HRID 378216 reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3([CH3:29])[C:18]4[CH:19]=[C:20]([CH:23]=[CH:24][C:25]([O:27]C)=[O:26])[CH:21]=[CH:22][C:17]=4[O:16][CH2:15]3)[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+].Cl>C1COCC1>[CH3:1][C:2]1([CH3:30])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]3([CH3:29])[C:18]4[CH:19]=[C:20]([CH:23]=[CH:24][C:25]([OH:27])=[O:26])[CH:21]=[CH:22][C:17]=4[O:16][CH2:15]3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70191371HCID 70191371, compound

Product 1

HCID 54110933HCID 54110933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-3-methyl-2,3-dihydrobenzofuran-5-yl]acrylate (330 mg, 0.79 mmol), a 2N methanolic sodium hydroxide solution (4 ml, 7.9 mmol) in THF (3 ml) is heated for 5 hours at 60° C. The mixture is acidified to pH 1 with a concentrated hydrochloric acid solution, extracted with ethyl acetate and washed with water. After drying the organic phase is concentrated in vacuo at 40° C. in a rotary evaporator, the product is purified by flash chromatography on a silica column.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. customAfter drying the organic phase
  4. concentrationis concentrated in vacuo at 40° C. in a rotary evaporator
  5. customthe product is purified by flash chromatography on a silica column

Sources & evidence

ORD record
ord-af7c4955cd5e418dadd95851191c1419
Source dataset
uspto-grants-2000_02
Patent number
US06030952

Reaction notes

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