Tributylstannane → HCID 86743468, compound

HRID 2352148Notes

Reaction equation

HRID 2352148 reaction equation
[CH3:1][C:2]([CH3:9])([C:7]#[CH:8])[CH2:3][C:4]([OH:6])=[O:5].[CH3:10][CH2:11][CH2:12][CH2:13][SnH:14]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH2:17][CH3:18].B(CC)(CC)CC.[F:30][C:31]1[C:36]([F:37])=[CH:35][C:34]([F:38])=[C:33]([F:39])[C:32]=1O.C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:9])([CH:7]=[CH:8][Sn:14]([CH2:13][CH2:12][CH2:11][CH3:10])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][C:32]1[C:31]([F:30])=[C:36]([F:37])[CH:35]=[C:34]([F:38])[C:33]=1[F:39])=[O:5]

Participants

7

Reactant 5

HCID 5948TributylstannaneHCID 7357TriethylboraneHCID 10868DicyclohexylcarbodiimideHCID 698582,3,5,6-TetrafluorophenolHCID 2986533,3-dimethylpent-4-ynoic acid

Product 1

HCID 86743468HCID 86743468, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3,3-dimethyl-4-pentynoic acid (20 mg, 0.16 mmol) in toluene (0.30 mL) under N2 was added Bu3SnH (0.10 mL, 0.38 mmol) followed by Et3B (0.03 mL, 1.0 M solution in hexanes, 0.03 mmol). The resulting solution was stirred at room temperature for 21/2 hours after which the solvent was evaporated under reduced pressure. The resulting oil was dissolved in anhydrous THF (0.32 mL) and 2,3,5,6-tetrafluorophenol (60 mg, 0.36 mmol) followed by dicyclohexylcarbodiimide (68 mg, 033 mmol) were added. The resulting solution was stirred at room temperature overnight during which time a white precipitate formed. The THF was evaporated under reduced pressure and the residue was suspended in CH3CN. The insoluble precipitate was filtered off and the filtrate was purified via flash chromatography (silica gel, 10 mm×160 mm, 2% EtOAc/hexanes) to afford 41 mg (45%) of 2,3,5,6-tetrafluorophenyl 3,3-dimethyl-5-(tri-n-butylstannyl)- 4-pentenoate as a mixture of isomers.

Workup

  1. customwas evaporated under reduced pressure
  2. dissolutionThe resulting oil was dissolved in anhydrous THF (0.32 mL)
  3. additionwere added
  4. stirringThe resulting solution was stirred at room temperature overnight during which time a white precipitate
  5. customformed
  6. customThe THF was evaporated under reduced pressure
  7. filtrationThe insoluble precipitate was filtered off
  8. customthe filtrate was purified via flash chromatography (silica gel, 10 mm×160 mm, 2% EtOAc/hexanes)

Sources & evidence

ORD record
ord-21317f1021204eaeada27177d1acb815
Source dataset
uspto-grants-1989_10
Patent number
US04876081

Reaction notes

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