Water → HCID 23503277, compound

HRID 1835172Notes

Reaction equation

HRID 1835172 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[C:9]([C:24]([OH:26])=[O:25])=[CH:10][S:11][C:12]=1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1.[CH:27]1([CH2:30][C:31](N(OC)C)=[O:32])[CH2:29][CH2:28]1.O>O1CCCC1>[CH:27]1([CH2:30][C:31]([C:10]2[S:11][C:12]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=3)=[C:8]([O:7][CH3:6])[C:9]=2[C:24]([OH:26])=[O:25])=[O:32])[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 224737662-cyclopropyl-N-methoxy-N-methylacetamideHCID 23503228HCID 23503228, compoundHCID 178418339Butyllithium

Product 1

HCID 23503277HCID 23503277, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2M butyl lithium in hexanes (1.75 ml) was added slowly to a solution of 4-methoxy-5-[(3-trifluoromethylphenyl)methyl]thiophene-3-carboxylic acid (500 mg) in tetrahydrofuran (30 ml) at −78° C. The resultant red solution was stirred for 20 minutes and then 2-cyclopropyl-N-methoxy-N-methylacetamide (229 mg) in tetrahydrofuran (3 ml) was added. The mixture was stirred for 20 minutes at −78° C. and was then allowed to warm to room temperature. After 5 hours water was added and the mixture was extracted with ethyl acetate. The organic phase was dried and concentrated. Purification of the residue by chromatography, eluting with 10:10:1 isohexane:ether:acetic acid, gave the sub-title compound (177 mg).

Workup

  1. stirringThe mixture was stirred for 20 minutes at −78° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customPurification of the residue by chromatography
  6. washeluting with 10:10:1 isohexane

Sources & evidence

ORD record
ord-a087e9832b224938b1bc346f2f791e3b
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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