Ethanethiol → HCID 60128070, compound

HRID 1454025Notes

Reaction equation

HRID 1454025 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]([CH3:17])[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]([CH3:17])[C:13]([O:15][CH3:16])=[O:14])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 60128074HCID 60128074, compound

Product 1

HCID 60128070HCID 60128070, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of methyl (2S)-2-[(1S)-5methoxy-2,3-dihydro-1H-inden-1yl]propanoate (Example 11) (5.70 g, 0.024 mol) in CH2Cl2 (70 mL), under argon, was cooled to 0-5° C. and AlCl3 (16.22 g, 0.122 mol) was added portion-wise while maintaining the temperature below 10° C. To this mixture was added EtSH (9.0 mL, 0.122 mol) and the resulting mixture was stirred at 0-5° C. for 4 h. The reaction mixture was then slowly poured into vigorously stirred ice-water (200 mL) and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with water, brine, dried (Na2SO4), filtered, and concentrated to dryness under vacuum. The resulting crude product was purified by silica gel flash chromatography (gradient of 10-40% ethyl acetate/hexanes) to give 4:2 g (80%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 6.93 (d, 1H), 6.70 (s, 1H), 6.63 (dd, 1H), 3.72 (s, 3H), 3.50 (q, 1H), 2.83 (m, 3H), 2.19 (m, 1H), 1.90 (m, 1H), 1.08 (d, 3H); LC-MS: RT=8.60 min, (M+H)+ 220.

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under vacuum
  7. customThe resulting crude product was purified by silica gel flash chromatography (gradient of 10-40% ethyl acetate/hexanes)
  8. customto give 4

Sources & evidence

ORD record
ord-50f807e519c547f391fa7c22181b8fab
Source dataset
uspto-grants-2009_01
Patent number
US07476742B2

Reaction notes

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