Allyl Alcohol → HCID 15819196, compound

HRID 1463566Notes

Reaction equation

HRID 1463566 reaction equation
[CH2:1]([O:3][P:4]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)(Cl)=[O:5])[CH3:2].[CH2:18]([OH:21])[CH:19]=[CH2:20].C(N(CC)CC)C>C(Cl)Cl.O>[F:17][C:14]([F:15])([F:16])[C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:21][CH2:18][CH:19]=[CH2:20]

Participants

6

Reactant 3

HCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 158191953-Trifluoromethylbenzylphosphonochloridic acid ethyl ester

Product 1

HCID 15819196HCID 15819196, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

The 3-trifluoromethylbenzylphosphonochloridic acid ethyl ester of Example 4 (0.2 g, 0.7 mmol) was dissolved in 20 mL of CH2Cl2 and added slowly at 0° C. to a mixture of 1.0 mmol of allyl alcohol and 1.0 of mmol triethylamine in 20 mL of CH2Cl2. The reaction mixture was stirred for 5 hours and then diluted with H2O. The aqueous phase was further extracted 3 times with CH2Cl2. The organic extracts were combined and, after drying with anhydrous Na2SO4, were evaporated to give the crude product as an oil. Purification by column chromatography on silica gel using ethyl acetate/hexane (2.5:1) yielded 0.14 g (63%) of analytically pure product as a colorless oil. D.C.I.M.S.[MH+ 309].

Workup

  1. extractionThe aqueous phase was further extracted 3 times with CH2Cl2
  2. dry with materialafter drying with anhydrous Na2SO4
  3. customwere evaporated
  4. customto give the crude product as an oil
  5. customPurification by column chromatography on silica gel
  6. customyielded 0.14 g (63%) of analytically pure product as a colorless oil

Sources & evidence

ORD record
ord-d1bb3ed85f3e4925819a3a510a2434a1
Source dataset
uspto-grants-1994_04
Patent number
US05300687

Reaction notes

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