1-Chloroethyl chloroformate → 2,3-Dihydrospiro(benzofuran-2,3'-piperidine)

HRID 1591161ノート

反応式

HRID 1591161 の反応式
C([N:8]1[CH2:13][CH2:12][CH2:11][C:10]2([CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClC(Cl)C>[NH:8]1[CH2:13][CH2:12][CH2:11][C:10]2([CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9]1

参加物

4

反応物 2

HCID 5213051-Chloroethyl chloroformateHCID 19045403HCID 19045403、化合物

生成物 1

HCID 190452922,3-Dihydrospiro(benzofuran-2,3'-piperidine)収率 94.2%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

A solution of 13 g (46 mmole) of 1'-benzyl-2,3-dihydrospiro(benzofuran-2,3'-piperidine) in 100 mL dichloroethane was treated with 7.13 g (5.2 mL, 51 mmoles) of 1-chloroethylchloroformate at room temperature for 1/2 hour. The reaction mixture was concentrated and the residue dissolved in CH3OH and heated to reflux for 1/2 hour. The methanol was evaporated at reduced pressure, and the residue partitioned between ethyl acetate and 1N HCl. The ethyl acetate layer was discarded and the aqueous phase was basified to pH 9 and reextracted with ethyl acetate. The ethyl acetate solution was dried over magnesium sulfate, filtered and concentrated in vacuo to give 8.2 g product.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in CH3OH
  3. temperatureheated
  4. temperatureto reflux for 1/2 hour
  5. customThe methanol was evaporated at reduced pressure
  6. customthe residue partitioned between ethyl acetate and 1N HCl
  7. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1c021af7f8244d2787829aaacebc1f2c
出典データセット
uspto-grants-1993_04
特許番号
US05206240

反応ノート

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