Water → HCID 178468872, compound

HRID 1035707Notes

Reaction equation

HRID 1035707 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][CH:6]([C:9]3[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=3)[CH2:5][CH2:4]2)[CH2:2]1.B(F)(F)F.CCOCC.O>ClCCl>[CH:2]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18][CH:19]=2)[CH2:5][CH2:4]1)=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 8000Boron trifluoride etherate2×HCID 86662113Ethyl 4-(1-oxaspiro[2.5]oct-6-yl)benzoate

Product 1

HCID 178468872HCID 178468872, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.4 g of ethyl 4-(1-oxaspiro[2.5]oct-6-yl)benzoate (5.38 mmol, 1.4 eq.) are placed in 40 mL of dichloromethane at 4° C. 0.229 g of boron trifluoride etherate (1.61 mmol, 0.3 eq.) is added with stirring. After 2 hours, 0.153 g of boron trifluoride etherate (1.07 mmol, 0.2 eq.) is added. After 1 hour, water is added and the reaction medium is extracted three times with dichloromethane. The organic phases are combined and washed successively with saturated aqueous sodium hydrogen carbonate solution and water. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on silica gel with an 88/10/2 mixture of heptane/ethyl acetate/methanol. 0.64 g of ethyl trans-4-(4-formylcyclohexyl)benzoate is obtained.

Workup

  1. waitAfter 1 hour
  2. extractionthe reaction medium is extracted three times with dichloromethane
  3. washwashed successively with saturated aqueous sodium hydrogen carbonate solution and water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on silica gel with an 88/10/2 mixture of heptane/ethyl acetate/methanol

Sources & evidence

ORD record
ord-1dec5afe689e4f9a80102dbc984cf48d
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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