Hydrochloric Acid → HCID 23563768, compound

HRID 1059001Notes

Reaction equation

HRID 1059001 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)[CH:9]=O)=[CH:4][CH:3]=1.[CH:25]([C:27]([CH3:29])=[O:28])=[CH2:26].[OH-].[K+].Cl>C1COCC1.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]4[CH2:21][CH2:22][CH2:23][CH2:24]4)[CH:12]=3)[CH2:26][CH2:25][C:27](=[O:28])[CH:29]=[CH:9]2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6570Methyl vinyl ketoneHCID 14797Potassium HydroxideHCID 18669682HCID 18669682, compound

Product 1

HCID 23563768HCID 23563768, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of 2-(4-bromophenyl)-2-(3-cyclopentyloxy-4-methoxyphenyl) acetaldehyde (2.60 g, 6.7 mmol) in THF (10 ml) was added methyl vinyl ketone (670 ul, 8.4 mmol). The solution was stirred at −10° C. and 10% ethanolic potassium hydroxide (480 ul) was added slowly. After 0.5 h the reaction mixture was warmed to room temperature and stirred for additional 1 h. Water and ethyl acetate were added and the mixture was neutralized with 3N hydrochloric acid. The layers were separated and the aqueous layer washed twice with ethyl acetate. The combined organic extract was washed with water then brine, dried (sodium sulfate) and evaporated. Purification by flash chromatography (silica gel, 12% ethyl acetate/82% hexane) provided the title compound as a pale white waxy solid (1.39 g, 47%). MS (m/e): 441 [(M+1)+], 443 [(M+3)+].

Workup

  1. temperatureAfter 0.5 h the reaction mixture was warmed to room temperature
  2. stirringstirred for additional 1 h
  3. customThe layers were separated
  4. washthe aqueous layer washed twice with ethyl acetate
  5. extractionThe combined organic extract
  6. washwas washed with water
  7. dry with materialbrine, dried (sodium sulfate)
  8. customevaporated
  9. customPurification by flash chromatography (silica gel, 12% ethyl acetate/82% hexane)

Sources & evidence

ORD record
ord-f6463d915f3941328ab79fe9e5469fab
Source dataset
uspto-grants-2003_02
Patent number
US06518306B1

Reaction notes

Loading…