Hexane → Benzofuran

HRID 457532Notes

Reaction equation

[CH3:1][CH2:2][O:3][C:4]([CH3:6])=O.[CH3:7][CH2:8][CH2:9][CH2:10]CC>>[O:3]1[C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[CH:1]=[CH:2]1

Participants

Reactant 2

HCID 8058Hexane

HCID 8857Ethyl Acetate

Product 1

HCID 9223BenzofuranYield 62.9%

Procedure

A solution of 30 (10.3 g; 39.3 mmol), EtOH (250 mL) and saturated NaHCO3 (100 mL) were heated to reflux for 1 h. The reaction mixture was cooled to room temperature and the EtOH removed in vacuo. Ice was added to the residue aqueous solution and the reaction carefully acidified to about pH 2 with 2 N HCl. The resulting mixture was extracted with EtOAc (2×300 mL) and the combined organic phase washed with brine, dried (NaSO4), filtered and evaporated to yield a brown oil (8.8 g). The crude product was run through a silica gel column with 15% EtOAc:hexane to yield 31 (5.44 g; 62.9%) as a white solid.

Sources & evidence

ORD record: ord-46109953725f4f0bb5bd72884658174d
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189718B2

Reaction notes

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