Water → 5-(Methoxymethoxy)-4-propyl-1,1-bis(trifluoromethyl)-1,3-dihydroisobenzofuran

HRID 552450Notes

Reaction equation

HRID 552450 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[C:11]([CH2:19][CH2:20][CH3:21])[C:10]=1[CH2:22]O)([OH:8])[C:4]([F:7])([F:6])[F:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O>ClCCl>[CH3:18][O:17][CH2:16][O:15][C:12]1[C:11]([CH2:19][CH2:20][CH3:21])=[C:10]2[C:9](=[CH:14][CH:13]=1)[C:3]([C:4]([F:6])([F:5])[F:7])([C:2]([F:1])([F:24])[F:25])[O:8][CH2:22]2

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 579007901,1,1,3,3,3-Hexafluoro-2-[2-(hydroxymethyl)-4-(methoxymethoxy)-3-propylphenyl]propan-2-ol

Product 1

HCID 579008265-(Methoxymethoxy)-4-propyl-1,1-bis(trifluoromethyl)-1,3-dihydroisobenzofuranYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1,1,3,3,3-hexafluoro-2-[2-(hydroxymethyl)-4-(methoxymethoxy)-3-propylphenyl]propan-2-ol (1.29 g, 3.43 mmol) and triphenylphosphine (1.98 g, 7.55 mmol) in dichloromethane (15 mL), diethyl azodicarboxylate (2.2 mol/L toluene solution, 4.67 mL, 10.27 mmol) was added under ice-cold conditions and the mixture was stirred overnight. The reaction solution was added with water and extracted with ethyl acetate. Subsequently, the organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated in vacuum. The residue was purified by silica-gel column chromatography (hexane/ethyl acetate) and the title compound (1.14 g, 93%) was obtained as colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washSubsequently, the organic layer was washed with saturated saline
  3. customdried
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-11a90613ca3847238136b87a132bb55e
Source dataset
uspto-grants-2011_05
Patent number
US07951822B2

Reaction notes

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