Water → HCID 178445646, compound

HRID 1674446Notes

Reaction equation

HRID 1674446 reaction equation
[CH:1]([CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])[CH2:7][CH2:6]1)=O.[CH3:21]C(C)([O-])C.[K+].O>C1COCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:4]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])[CH2:7][CH2:6]1)[CH2:3][CH:1]=[CH2:21]

Participants

6

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 178520639HCID 178520639, compound

Product 1

HCID 178445646HCID 178445646, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

7.0 g of 1-((trans-4-(2-formylethyl)cyclohexyl)methoxy)-2,3-difluorobenzene was dissolved in 30 mL of THF, and 10.6 g of methyl triphenylphosphonium bromide was added thereto. To this solution, the THF (15 mL) solution containing 3.3 g of potassium-t-butoxide was added dropwise at an internal temperature of 5 to 20° C., and the solution was stirred for 30 min. 10 mL of water was added thereto, and the solvent was evaporated under reduced pressure. Hexane and 50% methanol aqueous solution were added thereto, and the organic layer was fractioned. This organic layer was washed with 50% methanol aqueous solution and saturated saline, and subjected to column chromatography. The solvent was evaporated under reduced pressure, to thereby obtain 3.0 g of 1-((trans-4-(3-butenyl)cyclohexyl)methoxy)-2,3-difluorobenzene.

Workup

  1. additionwas added dropwise at an internal temperature of 5 to 20° C.
  2. customthe solvent was evaporated under reduced pressure
  3. additionHexane and 50% methanol aqueous solution were added
  4. washThis organic layer was washed with 50% methanol aqueous solution and saturated saline
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c4157de9c451400587df119694b2b4f0
Source dataset
uspto-grants-2011_08
Patent number
US08003006B2

Reaction notes

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