Hydrochloric Acid → HCID 67537665, compound

HRID 2240986Notes

Reaction equation

HRID 2240986 reaction equation
C(OP([CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[CH:20][CH:19]=2)[CH:11]=1)[F:9])OCC)C.[Li+].CC([N-]C(C)C)C.[CH:36]1([CH:39]=O)[CH2:38][CH2:37]1.Cl>O.C1COCC1>[CH:36]1([CH:39]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[C:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH:25]([F:26])[F:27])=[CH:22][CH:23]=3)[CH:11]=2)[F:9])[CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 123114CyclopropanecarboxaldehydeHCID 2724682Lithium diisopropylamideHCID 67537407HCID 67537407, compound

Product 1

HCID 67537665HCID 67537665, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a cold solution of diethyl[(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)(fluoro)methyl]phosphonite (2.0 g, 4.08 mmol) and THF (20 mL) was added dropwise LDA (14.64 mL, 1.0M). The mixture was stirred for 30 minutes and then cyclopropanecarbaldehyde (410 mg, 5.8 mmol) was added and the mixture was allowed to come to room temperature and stirred for 24 hours. Then, HCl (5 mL, 2N) was added and the mixture was stirred for 30 minutes, poured into water and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by ICSO (hexane/EtOAc 20/1) gavel-(2-cyclopropyl-1-fluorovinyl)-3-{[4-(difluoromethoxy)phenyl]ethynyl}benzene 1:1 Z/E isomers as a yellow oil (0.72 g); MS m/e (M)+ 328.

Workup

  1. customto come to room temperature
  2. stirringstirred for 24 hours
  3. stirringthe mixture was stirred for 30 minutes
  4. extractionextracted with EtOAc
  5. dry with materialThe organic extracts were dried over MgSO4
  6. customEvaporation and purification by ICSO (hexane/EtOAc 20/1)

Sources & evidence

ORD record
ord-9f4b6370f2da4351a0e72e1129651ace
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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