Ethanethiol → Methyl (2S)-2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]butanoate

HRID 1040259ノート

反応式

HRID 1040259 の反応式
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([C@H:12]([CH2:17][CH3:18])[C:13]([O:15][CH3:16])=[O:14])[CH2:7][CH2:6]2.[Al+3].[Cl-].[Cl-].[Cl-].CCS>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([C@H:12]([CH2:17][CH3:18])[C:13]([O:15][CH3:16])=[O:14])[CH2:7][CH2:6]2

参加物

5

反応物 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 12132838HCID 12132838、化合物

生成物 1

HCID 11183909Methyl (2S)-2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]butanoate収率 98.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a cold solution (ice water bath) of the compound prepared in Example 6 (233 g, 0.94 mol) in 2.5 L CH2Cl2, was added AlCl3 (630 g, 4.7 mol) slowly under Ar. The pot temperature was kept below 20° C., and the color of the reaction turned purple. EtSH (345 mL, 4.7 mol) was added slowly via an addition funnel to the reaction mixture, and the inside temperature was kept below 15° C. After 2 hours of stirring at below 20° C., the reaction went to completion by NMR analysis. The pot mixture was slowly poured into 2.5 L ice water with a strong agitation. The organic layer was separated, and the aqueous layer was extracted with 1 L CH2Cl2. The combined CH2Cl2 layers were washed with water (4×1 L) until pH 6.0-7.0, and then dried over Na2SO4. The product (216 g, 98%) was obtained as a white solid after solvent removal and vacuum drying. 1H NMR (DMSO-d6) δ 9.10(s, 1H), 6.78(d, 1H), 6.58(d, 1H), 6.50(dd, 1H), 3.60(s, 3H), 3.20(q, 1H), 2.70(m, 2H), 2.40(m, 1H), 2.08(m, 1H), 1.80(m, 1H), 1.50(m, 2H), 0.80(t, 3H).

後処理

  1. customwas kept below 20° C.
  2. customwas kept below 15° C
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with 1 L CH2Cl2
  5. washThe combined CH2Cl2 layers were washed with water (4×1 L) until pH 6.0-7.0
  6. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-35f28dea8dbc4d28a6fadc27233349a3
出典データセット
uspto-grants-2013_10
特許番号
US08552203B2

反応ノート

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