Tetrahydrofuran → Isohexane ethyl acetate

HRID 496648Notes

Reaction equation

HRID 496648 reaction equation
Cl[C:2]1[CH:9]=[C:8](CO)C=[C:6](Cl)[C:3]=1[CH:4]=[O:5].[O:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>>[CH3:8][CH2:9][CH2:2][CH:3]([CH3:6])[CH3:4].[C:14]([O:13][CH2:17][CH3:16])(=[O:5])[CH3:15]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 102420322,6-Dichloro-4-hydroxymethylbenzaldehyde

Product 1

HCID 21882781Isohexane ethyl acetate

Procedure

21.0 mg (0.8 mmol) Phosporous tribromide was added to a stirred solution of 480 mg (2.3 mmol) A3 in 20 ml dry tetrahydrofurane, and the solution was stirred for 3 hours at room temperature. After hydrolysis (15 ml) the phases were separated and the organic layer was washed with saturated NaCl (10 ml) and dried over magnesium sulfate. 236 mg (0.9 mmol) A16 was obtained by column chromatography on SiGel (iso-hexane/ethyl acetate 9:1).

Workup

  1. customwere separated
  2. washthe organic layer was washed with saturated NaCl (10 ml)
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-5c82e57d2c9147c885c99e37cbca257a
Source dataset
uspto-grants-2005_09
Patent number
US06946471B2

Reaction notes

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