Tetrahydrofuran → 2-Chloroethanol
Reaction equation
[Cl:1][CH2:2][O:3][CH2:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2.C(N(CC)CC)C.C1C[O:25][CH2:24][CH2:23]1>>[Cl:1][CH2:2][O:3][CH2:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2.[Cl:1][CH2:23][CH2:24][OH:25]Participants
5
Procedure
A two neck Kjeldahl flask of 50 ml into which a stirrer was put was charged with 2.15 g (10 mmol) of 1-adamantylmethyl chloromethyl ether obtained in (1), 0.97 g (12 mmol) of 2-chloroethanol, 1.52 g (15 mmol) of triethylamine and dried THF, and it was equipped with a coiled condenser to reflux and stir the solution for 8 hours. Triethylamine hydrochloride was filtered, and gas chromatographic analysis was carried out to find that chloroethyl chloromethyl ether was completely converted and that 2.25 g (8.7 mmol, isolation yield: 86.9%) of a colorless liquid which was the intended product was obtained at a selectivity of 98.5%.
Sources & evidence
- ORD record
- ord-896c2a56e2ce4803a49f68b40e94a665
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07402712B2
Reaction notes
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