HCID 20149485, compound → HCID 20149486, compound

HRID 568986Notes

Reaction equation

HRID 568986 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[F:5][C:6]([F:25])([CH:11]([N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[CH:12]=[CH2:13])[CH2:7][CH2:8][CH:9]=[O:10]>O1CCCC1>[OH:10][CH:9]([CH2:8][CH2:7][C:6]([F:5])([F:25])[CH:11]([N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[CH:12]=[CH2:13])[CH:1]=[CH2:2]

Participants

4

Reactant 2

HCID 20149485HCID 20149485, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 20149486HCID 20149486, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

Under an atmosphere of nitrogen, vinyl magnesium bromide (1 ml of 1M solution in tetrahydrofuran) is added to 4,4-difluoro-5-phthalimido-6-hepten-1-al (274 mg, 0.93 mmoles), dissolved in dry tetrahydrofuran (5 ml) previously cooled to -70° C. The temperature is allowed to rise to -5° C., and the reaction mixture is quenched with a saturated solution of ammonium chloride, diluted with ether, and the layers are separated. The alcohol obtained as an oil (300 mg) is purified by chromatography on silica (ethyl acetate/petroleum ether: 70/30, RF: 0.61): 148 mg (49%).

Workup

  1. customto rise to -5° C.
  2. customthe reaction mixture is quenched with a saturated solution of ammonium chloride
  3. additiondiluted with ether
  4. customthe layers are separated

Sources & evidence

ORD record
ord-ab74cb5304974f6ab4b97c4368a2ffa9
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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