1-Thiophen-2-yl-cyclohept-4-enecarboxylic acid ethyl ester → 1-Thiophen-2-yl-cycloheptanecarboxylic acid ethyl ester

HRID 2192308Notes

Reaction equation

HRID 2192308 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[H][H]>C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[CH2:1]([O:3][C:4]([C:6]1([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 583483311-Thiophen-2-yl-cyclohept-4-enecarboxylic acid ethyl esterHCID 178418361HCID 178418361, compound3×

Product 1

HCID 583483241-Thiophen-2-yl-cycloheptanecarboxylic acid ethyl esterYield 86.7%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)Catalyst3×HCID 702EthanolSolvent

Procedure

1-Thiophen-2-yl-cyclohept-4-enecarboxylic acid ethyl ester (Example 5b) (2.86 g) was dissolved in ethanol (30 mL) and tris(triphenylphosphine)rhodium(I) chloride (0.100 g) was added. The reaction mixture was stirred rapidly under 5 atmospheres of hydrogen overnight. Further tris(triphenylphosphine)rhodium(I) chloride (0.050 g) was added and the reaction mixture was stirred under 5 atmospheres of hydrogen for 3 days. A third addition of tris(triphenylphosphine)rhodium(I) chloride (0.050 g) was made and the reaction mixture was stirred under 3 atmospheres of hydrogen overnight. The contents were evaporated to dryness and purified on silica eluting with ethyl acetate/isohexane (5/ 95) to afford the sub-titled compound (2.500 g) as a clear almost colourless oil

Workup

  1. customThe contents were evaporated to dryness
  2. custompurified on silica eluting with ethyl acetate/isohexane (5/ 95)

Sources & evidence

ORD record
ord-6472a42849174177afd228c2e2c320f5
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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