3-Methylbut-1-yne → 6-Methoxy-2-(1-methylethyl)benzofuran

HRID 985203Notes

Reaction equation

HRID 985203 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].[CH3:11][CH:12]([CH3:15])[C:13]#[CH:14]>>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[CH:14]=[C:13]([CH:12]([CH3:15])[CH3:11])[O:10][C:3]=2[CH:4]=1

Participants

3

Reactant 2

HCID 690193-Methylbut-1-yneHCID 114140152-Iodo-5-methoxyphenol

Product 1

HCID 107977526-Methoxy-2-(1-methylethyl)benzofuranYield 38%

Procedure

Example 15(a) was prepared from 2-iodo-5-methoxyphenol (896 mg, 3.6 mmole) and 3-methyl-1-butyne in a manner as previously described for example 12a to give 265 mg (38%) of an amber oil. 1H NMR (CDCl3) δ7.33 (1H, d, J=8.6 Hz), 6.97 (1H, d, J=2.2 Hz), 6.80 (1H, dd, J=2.2, 8.6 Hz), 6.26 (1H, s), 3.83 (3H, s), 3.07-3.01 (1H, m), 1.31 (6H, d, J=7.1 Hz).

Sources & evidence

ORD record
ord-518ea7c16c794617a9f2ad4133b8f55d
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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