Sodium Hypochlorite → Benzyl 3a,4-dihydro-3H-pyrrolo[3,4-c]isoxazole-5(6H)-carboxylate

HRID 77569ノート

反応式

HRID 77569 の反応式
[CH2:1]([N:4]([CH2:15][CH:16]=[N:17][OH:18])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3].Cl[O-].[Na+]>ClCCl>[N:17]1[O:18][CH2:3][CH:2]2[CH2:1][N:4]([C:5]([O:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:14])[CH2:15][C:16]=12

参加物

4

反応物 2

HCID 23665760Sodium HypochloriteHCID 74074414Benzyl N-allyl-N-[2-hydroxyiminoethyl]carbamate

生成物 1

HCID 86697896Benzyl 3a,4-dihydro-3H-pyrrolo[3,4-c]isoxazole-5(6H)-carboxylate収率 75.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of Benzyl N-allyl-N-[2-hydroxyiminoethyl]carbamate (24 g, 96.6 mmol) in dichloromethane (338 mL) is treated drop wise over 10 minutes with a 5% w/w aqueous solution of sodium hypochlorite (106.08 mmol, 143.06 mL). The resultant mixture is stirred at room temperature overnight. The reaction is quenched with a 40% aqueous solution of sodium bisulfite (7 g). The organic layer is separated, dried over magnesium sulfate, and concentrated under vacuum. The crude product is purified over silica gel eluting with 5% ethyl acetate in hexanes to give the title compound (18 g, 75%). ES/MS (m/e): 247 (M+H).

後処理

  1. customThe reaction is quenched with a 40% aqueous solution of sodium bisulfite (7 g)
  2. customThe organic layer is separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product is purified over silica gel eluting with 5% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-79559e19ee9047a3b0264ef612760d7f
出典データセット
uspto-grants-2014_09
特許番号
US08841293B1

反応ノート

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