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Methanol → 3-(3-{2-[3-(3-Hydroxy-2,2-dimethylpropyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethylpropan-1-ol

HRID 239070
ノート
印刷プレビュー

反応式

HRID 239070 の反応式
[Li+].[BH4-].CO.C([O:7][C:8](=O)[C:9]([CH3:39])([CH3:38])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30]([C:33](OCC)=[O:34])([CH3:32])[CH3:31])[CH:24]=3)[S:22][CH2:21][CH2:20][CH2:19][S:18]2)[CH:12]=1)C.[NH4+].[Cl-]>C(Cl)Cl>[OH:7][CH2:8][C:9]([CH3:39])([CH3:38])[CH2:10][C:11]1[CH:12]=[C:13]([C:17]2([C:23]3[CH:24]=[C:25]([CH2:29][C:30]([CH3:32])([CH3:31])[CH2:33][OH:34])[CH:26]=[CH:27][CH:28]=3)[S:18][CH2:19][CH2:20][CH2:21][S:22]2)[CH:14]=[CH:15][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 113185153-(3-{2-[3-(2-Ethoxycarbonyl-2-methyl-propyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethyl-propanoic acid ethyl ester

生成物 1

HCID 114649623-(3-{2-[3-(3-Hydroxy-2,2-dimethylpropyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethylpropan-1-ol収率 85.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of LiBH4 (0.78 g, 35.8 mmol) in CH2Cl2 (55 mL) was added methanol (1.04 g, 32.5 mmol) at room temperature. After the addition of 229 (6.5 g, 12.3 mmol), the reaction mixture was heated to reflux for 6 h. After cooling to room temperature, saturated aqueous NH4Cl solution (20 mL) and CH2Cl2 (15 mL) were added and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to afford 230 (4.66 g, 85%) as an oil. 1H NMR (CDCl3): δ 7.42 (s br., 2 H), 7.17 (m, 4 H), 6.97 (m, 2 H), 3.63 (s, 4 H), 3.16 (s, 4 H), 2.69 (m, 2 H), 2.47 (m, 4 H), 1.88 (m, 2 H), 0.75 (s, 12 H). 13C NMR (CDCl3): δ 142.39, 139.18, 131.69, 129.88, 128.05, 127.01, 71.12, 44.89, 43.74, 36.70, 29.63, 24.22.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×10 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c09087bfb0c44c84a21ca33a8af7d762
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08642653B2

反応ノート

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