Methanol → 2-Hydroxymethyl-3-methyl-5-methoxythiophene
Reaction equation
[OH:1][CH2:2][C:3]1[S:4][C:5](I)=[CH:6][C:7]=1[CH3:8].[Na].[CH3:11][OH:12]>>[OH:1][CH2:2][C:3]1[S:4][C:5]([O:12][CH3:11])=[CH:6][C:7]=1[CH3:8]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
10.0 G. (0.125 mol) of cupric oxide and 11.0 g. (0.0433 mol) of 2-hydroxymethyl-3-methyl-5-iodothiophene was added to a solution of 10.0 g. (0.435 mol) of sodium in 90 ml. of methanol. The resulting reaction mixture was heated to 80° C. for 18 hrs. with vigorous stirring. The cold solution was filtered, the filtrate poured into ice water and extracted with ether/hexane (ratio 4:1). The organic extracts were washed with 10% sodium thiosulfate solution and saturated sodium chloride solution, dried and evaporated to yield 2-hydroxymethyl-3-methyl-5-methoxythiophene as a colorless oil.
Workup
- customThe resulting reaction mixture
- filtrationThe cold solution was filtered
- additionthe filtrate poured into ice water
- extractionextracted with ether/hexane (ratio 4:1)
- washThe organic extracts were washed with 10% sodium thiosulfate solution and saturated sodium chloride solution
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-7e40177e4c3b45d8abbdc6bfc7bf231f
- Source dataset
- uspto-grants-1980_10
- Patent number
- US04230872
Reaction notes
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