HCID 57691462, compound → HCID 57691453, compound

HRID 1867645Notes

Reaction equation

HRID 1867645 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[O:31])[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=1.[CH:32]([Mg]Br)=[CH2:33]>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([OH:31])([CH:32]=[CH2:33])[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:20]=[C:19]([C:27]([F:28])([F:29])[F:30])[CH:18]=1

Participants

4

Reactant 2

HCID 57691462HCID 57691462, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 57691453HCID 57691453, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of 1-(2-(1,3-dioxan-2-yl)phenyl)-2-(3,5-bis(trifluoromethyl)benzyloxy)ethanone (1.06 g, 2.36 mmol) in tetrahydrofuran (15 mL) at −78° C. was added vinylmagnesium bromide (1 M in tetrahydrofuran, 4.73 mL, 4.73 mmol). The reaction was allowed to warm to −60° C. in the Dewar flask before quenching with saturated ammonium chloride. The reaction was poured into diethyl ether, washed with water, then brine, dried over magnesium sulfate, and concentrated. Column chromatography (12%-->25% EtOAc/Hex) gave 810 mg (72%) as a colorless oil. Mass spec.: 499.30 (MNa)+.

Workup

  1. custombefore quenching with saturated ammonium chloride
  2. additionThe reaction was poured into diethyl ether
  3. washwashed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customColumn chromatography (12%-->25% EtOAc/Hex) gave 810 mg (72%) as a colorless oil

Sources & evidence

ORD record
ord-777ffb0228f94f9c817da898707c44a1
Source dataset
uspto-grants-2009_12
Patent number
US07632861B2

Reaction notes

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