Ethanethiol → Ethyl (S)-4-(hydroxyphenyl)-3-(pyridin-3-yl)butanoate

HRID 1816012Notes

Reaction equation

HRID 1816012 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1.C(S)C.[Al+3].[Cl-].[Cl-].[Cl-].C([O-])(O)=[O:31].[Na+]>C(Cl)Cl>[OH:31][C:7]1[CH:8]=[CH:3][CH:4]=[CH:5][C:6]=1[CH2:9][C@H:10]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 59997619Ethyl (S)-4-(4-methoxyphenyl)-3-(pyridin-3-yl)butanoate

Product 1

HCID 86759664Ethyl (S)-4-(hydroxyphenyl)-3-(pyridin-3-yl)butanoateYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl (S)-4-(4-methoxyphenyl)-3-(pyridin-3-yl)butanoate (9.25 g, 31 mmole) in CH2Cl2 (150 mL) was cooled to 0° C. Ethanethiol (11.5 mL, 155 mmole) was added, then AlCl3 (20.7 g, 155 mmole) was added portionwise. After 2 hr, the mixture was poured over ice, allowed to warm to RT, and neutralized with NaHCO3. The resulting suspension was filtered through celite® and the filter pad was washed with CH2Cl2. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated. Flash chromatography on silica gel (1:1 EtOAc/hexanes) afforded the title compound (6.435 g, 73%) 1H NMR (400 MHz, CDCl3) δ 8.72, 8.41 (dd, J=4.9, 1.5 Hz, 1 H), 8.24 (narrow m, 1 H), 7.26 (dd, J=7.8, 4.9 Hz, 1 H). 6.78 (d, J=8.5 Hz, 2 H), 6.64 (d, J=8.5 Hz, 2 H), 4.03 (q, J=7.1 Hz, 2 H), 3.34-3.48 (m, 1 H), 2.92 (dd, J=13.7, 6.1 Hz, 1 H). 2.69-2.81 (m, 2 H), 2.64 (dd, J=15.6, 8.7 Hz, 1 H), 1.13 (t, J=7.1 Hz, 3 H); MS (ES) m/e 286 (M+H)+.

Workup

  1. additionthe mixture was poured over ice
  2. filtrationThe resulting suspension was filtered through celite®
  3. washthe filter pad was washed with CH2Cl2
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with CH2Cl2
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5207fca5c0d4499691b04b2ea3f207af
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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