4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propenyl]-benzoic acid → 4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-benzoic acid

HRID 2261445Notes

Reaction equation

HRID 2261445 reaction equation
[O:1]=[C:2]([C:14]1[S:21][C:20]([CH3:22])=[C:19]2[C:15]=1[CH2:16][C@H:17]1[C:23]([CH3:25])([CH3:24])[C@H:18]12)[CH:3]=[CH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1>C(O)C.C1COCC1.[Pd]>[O:1]=[C:2]([C:14]1[S:21][C:20]([CH3:22])=[C:19]2[C:15]=1[CH2:16][C@H:17]1[C:23]([CH3:25])([CH3:24])[C@H:18]12)[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([OH:11])=[O:10])=[CH:12][CH:13]=1

Participants

5

Reactant 1

HCID 674155074-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propenyl]-benzoic acid

Product 1

HCID 674156284-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-benzoic acidYield 95.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propenyl]-benzoic acid (780 mg, 2.21 mmol), Pd/C (250 mg, 10% Pd) in ethanol (50 mL) and THF (10 mL) is stirred at rt for 2 h under 1.5 bar H2. The reaction mixture is filtered, the filtrate is evaporated and the crude product is purified by CC on silica gel eluting with EA to give 4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-benzoic acid (751 mg) as a colourless foam; LC-MS: tR=1.04 min, [M+1]+=355.08; 1H NMR (CDCl3): δ 8.02 (d, J=7.6 Hz, 2H), 7.32 8d, J=7.6 Hz, 2H), 3.12-2.90 (m, 5H), 2.77 (d, J=18.8 Hz, 1H), 2.37 (s, 3H), 1.92-1.86 (m, 2H), 1.11 (s, 3H), 0.69 (s, 3H).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated
  3. customthe crude product is purified by CC on silica gel eluting with EA

Sources & evidence

ORD record
ord-a03d44744f4b4de5b465e081297ffcf0
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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