Carbon Dioxide → HCID 54084237, compound

HRID 2289424Notes

Reaction equation

HRID 2289424 reaction equation
[CH2:1]([NH:5][C:6]([CH:8]=[C:9]1[C:17]2[CH:16]=[CH:15][S:14][C:13]=2[CH2:12][CH2:11][CH2:10]1)=[O:7])[CH2:2][CH2:3][CH3:4].C1COCC1.C([Li])CCC.[C:28](=[O:30])=[O:29]>CCCCCC.O.CCOCC>[CH2:1]([NH:5][C:6]([CH:8]=[C:9]1[C:17]2[CH:16]=[C:15]([C:28]([OH:30])=[O:29])[S:14][C:13]=2[CH2:12][CH2:11][CH2:10]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 54044452HCID 54044452, compoundHCID 178418339Butyllithium

Product 1

HCID 54084237HCID 54084237, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

To a mixture of 4-(N-butylcarbamoyl)methylidene-4,5,6,7-tetrahydrobenzo[b]thiophene (0.49 g) and THF (8 ml) was dropwise added 1.64 M n-butyl lithium (n-BuLi) in n-hexane (2.88 ml) at -70~-60° C. under nitrogen atmosphere and the mixture was stirred under the same condition for 2.5 hours. The reaction mixture was poured into a mixture of dry ice and diethyl ether (Et2O). To the mixture were added Et2O and water. The separated aqueous layer was washed with Et2O, and acidified by 6 N hydrochloric acid (HCl) and was extracted with AcOEt. The organic layer was washed with water and brine, and dried over MgSO4, and evaporated in vacuo to give 4-(N-butylcarbamoyl)methylidene-4,5,6,7-tetrahydrobenzo[b]-thiophene-2-carboxylic acid (0.38 g).

Workup

  1. customat -70~-60° C.
  2. washThe separated aqueous layer was washed with Et2O
  3. extractionwas extracted with AcOEt
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-98068ccfca504cb9bfb22e6cbc6e1a12
Source dataset
uspto-grants-2000_07
Patent number
US06093710

Reaction notes

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