Thionyl Chloride → tert-Butyl [4-(chloromethyl)phenyl]carbamate

HRID 2067334ノート

反応式

HRID 2067334 の反応式
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1.S(Cl)([Cl:19])=O>ClCCl.N1C=CC=CC=1>[Cl:19][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1

参加物

5

反応物 2

HCID 24386Thionyl ChlorideHCID 10242688Boc-4-aminobenzylalcohol

生成物 1

HCID 46835249tert-Butyl [4-(chloromethyl)phenyl]carbamate収率 50%

試薬・触媒・溶媒 2

HCID 1049Pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of tert-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g, 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL, 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL), and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 4-(chloromethyl)-phenylcarbamate as an orange solid in 50% yield (0.27 g, 50%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 6.51 (br s, 1H), 4.55 (s, 2H), 1.52 (s, 9H).

後処理

  1. customThe resulting reaction mixture
  2. customquenched with water (25 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (50 mL)
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3e98fc89cd874f068a4dfc2132c2176b
出典データセット
uspto-grants-2012_10
特許番号
US08293768B2

反応ノート

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