Hydrochloric Acid → HCID 57691458, compound

HRID 1867646Notes

Reaction equation

HRID 1867646 reaction equation
[O:1]1CCC[O:3][CH:2]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](O)([CH:31]=[CH2:32])[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.Cl>CC(C)=O.O>[F:29][C:27]([F:28])([F:30])[C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:20]=1)[CH2:16][O:15][CH2:14][C:13]1([CH:31]=[CH2:32])[C:8]2[C:7](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:2]([OH:1])[O:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57691453HCID 57691453, compound

Product 1

HCID 57691458HCID 57691458, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(2-(1,3-dioxan-2-yl)phenyl)-1-(3,5-bis(trifluoromethyl)benzyloxy)but-3-en-2-ol (800 mg, 1.68 mmol) in acetone (20 mL) and water (1 mL) was added concentrated hydrochloric acid (0.2 mL) at room temperature. The resulting reaction was stirred at room temperature for 2 h. The reaction was quenched by addition of saturated sodium bicarbonate, and concentrated to remove most of the acetone. The mixture was poured into diethyl ether, washed with water, then brine, dried over magnesium sulfate, and concentrated. Column chromatography (25%-->50% EtOAc/Hex) gave 475 mg (68%) as a colorless oil. Mass spec.: 401.32 (M-OH)+.

Workup

  1. customThe resulting reaction
  2. customThe reaction was quenched by addition of saturated sodium bicarbonate
  3. concentrationconcentrated
  4. customto remove most of the acetone
  5. additionThe mixture was poured into diethyl ether
  6. washwashed with water
  7. dry with materialbrine, dried over magnesium sulfate
  8. concentrationconcentrated
  9. customColumn chromatography (25%-->50% EtOAc/Hex) gave 475 mg (68%) as a colorless oil

Sources & evidence

ORD record
ord-d16e99e8f7f84cf591635c0f9bccbfa5
Source dataset
uspto-grants-2009_12
Patent number
US07632861B2

Reaction notes

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