Diethyl Ether → 3-(4-Benzyloxyphenyl)-1-cyclopentylpropan-1-one

HRID 858750ノート

反応式

HRID 858750 の反応式
N1C=CC=CC=1S[C:8](=[O:25])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1.[CH:26]1([Mg]Br)[CH2:30][CH2:29][CH2:28][CH2:27]1.CCOCC>C1COCC1>[CH2:18]([O:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][C:8]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:25])=[CH:16][CH:15]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 210622503-(4-Benzyloxyphenyl)thiopropionic Acid S-pyridin-2-yl EsterHCID 178419650HCID 178419650、化合物

生成物 1

HCID 219384933-(4-Benzyloxyphenyl)-1-cyclopentylpropan-1-one収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

3-(4-Benzyloxyphenyl)thiopropionic acid S-pyridin-2-yl ester (3.00 g, 8.58 mmol) from Step 4 above was dissolved in dry THF (45 mL) and cooled to −78° C. A solution of cyclopentylmagnesium bromide in Et2O (2.0 M, 4.51 mL, 9.02 mmol) was added dropwise along the sides of the reaction vessel. After stirring 35 min, the cooling bath was removed. The reaction mixture was quenched with saturated aq. NH4Cl upon reaching ambient temperature and extracted with Et2O (500 mL). The organic phase was washed with brine (50 mL), dried over MgSO4 and evaporated. The residue was purified by flash column chromatography (10% EtOAc in hexanes) to give the product (2.22 g, 84%) as a white semi-crystalline material.

後処理

  1. customthe cooling bath was removed
  2. customThe reaction mixture was quenched with saturated aq. NH4Cl
  3. customupon reaching ambient temperature
  4. extractionextracted with Et2O (500 mL)
  5. washThe organic phase was washed with brine (50 mL)
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-ed1cb50e605e49c29ab7ce141b245697
出典データセット
uspto-grants-2006_12
特許番号
US07148226B2

反応ノート

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