Oxetane → α-Ethyl-5-methyl-2-thiophenemethanol

HRID 359749Notes

Reaction equation

HRID 359749 reaction equation
[Li+].CCC[CH2-].[CH3:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.[O:12]1[CH2:15][CH2:14][CH2:13]1.[Cl-].[NH4+]>CCCCCC.C1COCC1>[CH3:6][C:7]1[S:8][C:9]([CH:15]([OH:12])[CH2:14][CH3:13])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 10423OxetaneHCID 111262-MethylthiopheneHCID 25517Ammonium ChlorideHCID 61028n-Butyl lithium

Product 1

HCID 19780497α-Ethyl-5-methyl-2-thiophenemethanolYield 17.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

N-Butyllithium in hexane (1.5M; 35.6 ml) was added dropwise at room temperature under nitrogen to a solution of 2-methylthiophene (5.0 g) in dry THF (50 ml). After stirring for 2.25 h, oxetane (4.42 g) in dry THF (15 ml) was added dropwise and stirring continued for 22.5 h. Saturated ammonium chloride solution (200 ml) was added and the mixture extracted with diethyl ether (3×200 ml), dried and evaporated in vacuo to give an oil. Purification by FCC on silica gel with cyclohexane-diethyl ether (1:1) as eluent gave the title compound as a pale orange oil (1.4 g). T.l.c. (cyclohexane-diethyl ether 1:1) Rf 0.31.

Workup

  1. stirringstirring
  2. waitcontinued for 22.5 h
  3. extractionthe mixture extracted with diethyl ether (3×200 ml)
  4. customdried
  5. customevaporated in vacuo
  6. customto give an oil
  7. customPurification by FCC on silica gel with cyclohexane-diethyl ether (1:1) as eluent

Sources & evidence

ORD record
ord-94e69922e1744a8b9c6ce56a4c41268f
Source dataset
uspto-grants-1991_03
Patent number
US05002966

Reaction notes

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