Methanol → HCID 13409285, compound

HRID 1980540Notes

Reaction equation

HRID 1980540 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[C:16]2[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[CH3:27]S(O)(=O)=O>C(Cl)Cl>[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[C:16]2[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH3:27])=[O:23])[CH2:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 13409282HCID 13409282, compound

Product 1

HCID 13409285HCID 13409285, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 70.0 g (0.22 mol) of 4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylic acid (Example 1), 35.2 g (1.1 mol) of methanol, 350 mL of methylene dichloride, and 0.5 mL of methanesulfonic acid was heated under reflux for 21 h. The reaction mixture was cooled, washed with water, dried over sodium sulfate, concentrated in vacuo, and crystallized from ethyl acetate:hexane to give 51.8 g (71%) of methyl 4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylate in two crops: m.p. 175°-177° C.

Workup

  1. temperatureunder reflux for 21 h
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fc0f51c9b2a74b2c97ce1ac51651c5e8
Source dataset
uspto-grants-1985_04
Patent number
US04510158

Reaction notes

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