Water → HCID 53937349, compound

HRID 986336Notes

Reaction equation

HRID 986336 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]1([O:28][Si](C)(C)C)[C:16](=[CH:17][CH:18]=[C:19]([CH3:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[C:15](=[O:27])[CH:14]=[CH:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.O.C1(C)C=CC=CC=1>CC(O)=O>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]1([OH:28])[C:16](=[CH:17][CH:18]=[C:19]([CH3:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:24])[CH3:25])[C:15](=[O:27])[CH:14]=[CH:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 8028TetrahydrofuranHCID 54400631HCID 54400631, compound

Product 1

HCID 53937349HCID 53937349, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

50 mg (0.11 mmole) of 4-(4-phenoxybutyl)-4-trimethylsilyloxy-5-(3,7-dimethyl-2,6-octadienylidene)-2-cyclopentenone was dissolved in 10 ml of a mixture of AcOH:THF:H2O (=3:1:1), and the solution was stirred at 40° C. for 3 hours. After the reaction, toluene was added, and AcOH and water were distilled off under reduced pressure. The residue was chromatographed on a silica gel column (hexane:AcOET=1.5:1) to give 32 mg (75%) of the desired compound indicated above.

Workup

  1. additionwas added
  2. distillationAcOH and water were distilled off under reduced pressure
  3. customThe residue was chromatographed on a silica gel column (hexane:AcOET=1.5:1)

Sources & evidence

ORD record
ord-8f543ac229104a3389ef110af7681f54
Source dataset
uspto-grants-1987_12
Patent number
US04711895

Reaction notes

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