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

HRID 603377ノート

反応式

HRID 603377 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 22 (233 g, 0.94 mol) in CH2Cl2 (2.5 L), was added AlCl3 (630 g, 4.7 mol) slowly under argon. The internal 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 maintaining the internal temperature below 15° C. After 2 h of stirring at a temperature below 20° C., the reaction was completed and was slowly poured into ice-water (2.5 L) with strong agitation. The organic phase was separated, and the aqueous phases was extracted with CH2Cl2 (1 L) The combined organic phases were washed with water (4×1 L) until a pH of 6.0-7.0 was reached, and then dried over Na2SO4, filtered, concentrated under reduced pressure and then dried under vacuum to provide the title compound (216 g, 98%) as a white solid. 1H NMR (300 MHz), (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. temperaturemaintaining the internal temperature below 15° C
  3. customThe organic phase was separated
  4. extractionthe aqueous phases was extracted with CH2Cl2 (1 L) The combined organic phases
  5. washwere washed with water (4×1 L) until a pH of 6.0-7.0
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-aa392ca0fb7d4bd58755f8c1323ba36a
出典データセット
uspto-grants-2011_03
特許番号
US07906653B2

反応ノート

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