8-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene → 8-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decane

HRID 1025676Notes

Reaction equation

HRID 1025676 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.O=[Pt]=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][CH2:16][C:11]3([O:12][CH2:13][CH2:14][O:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 152326828-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

Product 1

HCID 128344048-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decaneYield 98%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 1140TolueneSolvent

Procedure

The intermediate from step A (8.8 g, 37.6 mmol) was dissolved in toluene and to it was added PtO2 (0.5 g). The resulting mixture was stirred under hydrogen at atmospheric pressure overnight. The catalyst was filtered off and the filtrate was removed under reduced pressure. Flash chromatography on silica gel eluting with 5% and then 10% EtOAc in hexanes provided the title compound (8.6 g, 98%) as an oil. MS calculated (M+H)+ 237, found 237.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-30f9362895e047c2bd2d22ca75061c9e
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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