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

HRID 1454029Notes

Reaction equation

HRID 1454029 reaction equation
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

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 12132838HCID 12132838, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold solution (ice water bath) of the compound prepared in Example 20 (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 was below 15° C. After 2 h of stirring at 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 pH 6.0-7.0, 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).

Workup

  1. customwas kept below 20° C.
  2. temperaturemaintaining the internal temperature
  3. customwas below 15° C
  4. customThe organic phase was separated
  5. extractionthe aqueous phases was extracted with CH2Cl2 (1 L)
  6. washThe combined organic phases were washed with water (4×1 L) until pH 6.0-7.0
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customdried under vacuum

Sources & evidence

ORD record
ord-352bceacc8ef4adfaded7f3fda7c0461
Source dataset
uspto-grants-2009_01
Patent number
US07476742B2

Reaction notes

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