Tetrahydrofuran → Isohexane ethyl acetate

HRID 1006469Notes

Reaction equation

HRID 1006469 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-d69bf4056ac243c183345f4749a93900
Source dataset
uspto-grants-2004_09
Patent number
US06790852B2

Reaction notes

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