Water → (6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-yl)methyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 2164854Notes

Reaction equation

HRID 2164854 reaction equation
[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]([CH2:16][OH:17])=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:25][C:26]([F:36])=[CH:27][C@H:28]1[C@H:30]([C:31](Cl)=[O:32])[C:29]1([CH3:35])[CH3:34].O>C(OCC)C>[F:25][C:26]([F:36])=[CH:27][C@H:28]1[C@H:30]([C:31]([O:17][CH2:16][C:4]2[C:5]3[CH2:11][CH2:10][CH2:9][C:8]4[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=4[C:6]=3[CH:1]=[CH:2][CH:3]=2)=[O:32])[C:29]1([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 20259244HCID 20259244, compoundHCID 86740007trans-3-(2,2-Difluoroethenyl)-2,2-dimethylcyclopropanecarbonylchloride

Product 1

HCID 70479757(6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-yl)methyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-methanol (0.95 g, 0.043 mole) and 1 ml of dry triethylamine in 15 ml of dry diethyl ether was added 3 ml of a solution of trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride in dry diethyl ether (1.42 mmole/ml). The resultant mixture was stirred at room temperature for approximately 18 hours, then poured into 50 ml of water. The organic phase was separated and washed first with an aqueous 5% sodium bicarbonate solution and then with water. The organic solution was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to leave an oil. This oil was purified by column chromatography on silica gel, eluted with ethyl acetate:hexanes (5:95), to yield 0.83 g of (6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-yl)methyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate as an oil.

Workup

  1. customThe organic phase was separated
  2. washwashed first with an aqueous 5% sodium bicarbonate solution
  3. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. customto leave an oil
  7. customThis oil was purified by column chromatography on silica gel
  8. washeluted with ethyl acetate:hexanes (5:95)

Sources & evidence

ORD record
ord-2e6fd739966e4facad20eca44fed674b
Source dataset
uspto-grants-1985_03
Patent number
US04507317

Reaction notes

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