HCID 59032875, compound → HCID 59032880, compound

HRID 1634380Notes

Reaction equation

HRID 1634380 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](/[C:17](/[F:34])=[C:18](\[F:33])/[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:21]=2)[CH2:9][CH:10](O)[CH2:11][Si](C)(C)C)=[CH:4][CH:3]=1>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:9][CH:10]=[CH2:11])/[C:17](/[F:34])=[C:18](\[F:33])/[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:21]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 59032875HCID 59032875, compound

Product 1

HCID 59032880HCID 59032880, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 176Acetic AcidSolvent

Procedure

(5E )-4-(4-chlorophenyl)-5,6-difluoro-7-(3-phenoxyphenyl)-1-(trimethylsilyl)-5-hepten-2-ol (0.194 g, 0.39 mmol) was dissolved in glacial acetic acid (8 ml) containing water (40 drops) and heated at 105° C. to 110° C. for six hours. The reaction mixture was concentrated in vacuo, the residue diluted with saturated aqueous so dium bicarbonate, and extracted with methylene chloride (3×25 ml). The combined organic extracts were washed with water (25 ml), dried over anhydrous sodium sulfate and concentrated in vacuo to a yellow oil (0.16 g). Chromatography an a preparative thin layer silica gel plate developing with methylene chloride:hexane (1:1) afforded the title compound as a colorless oil (0.151 g) which is characterized by IR, 1HNMR and mass spectral analysis.

Workup

  1. temperatureheated at 105° C. to 110° C. for six hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue diluted with saturated aqueous so dium bicarbonate
  4. extractionextracted with methylene chloride (3×25 ml)
  5. washThe combined organic extracts were washed with water (25 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo to a yellow oil (0.16 g)

Sources & evidence

ORD record
ord-b6e63d9f31c04029b070717388c17851
Source dataset
uspto-grants-2003_01
Patent number
US06506800B2

Reaction notes

Loading…