Water → 2-(3-Butynyloxy)tetrahydro-2H-pyran

HRID 17187

反応式

HRID 17187 の反応式
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>ClCCl>[CH2:1]([O:5][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1)[CH2:2][C:3]#[CH:4]

参加物

6

反応物 4

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 135663-Butyn-1-OLHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

生成物 1

HCID 1424402-(3-Butynyloxy)tetrahydro-2H-pyran収率 98%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of but-3-yn-1-ol (10.00 g, 143 mmol) in dichloromethane (310 mL) was treated with dihyropyran (18.10 g, 215 mmol) and pyridinium p-toluene sulfonate (3.60 g, 14.30 mmol). The reaction mixture was stirred at room temperature for 4 days. Water was added and the layers were partitioned. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The crude material was purified by flash chromatography on silica gel using 1:1 ethyl acetate: heptane to give 21.57 g (98%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 4.65 (m, 1H), 3.90-3.80 (m, 2H), 3.60-3.50 (m, 2H), 2.50-2.45 (m, 2H), 1.95 (m, 1H), 1.90-1.80 (m, 1H), 1.79-1.10 (m, 1H), 1.65-1.50 (m, 4H).

後処理

  1. customthe layers were partitioned
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude material was purified by flash chromatography on silica gel using 1:1 ethyl acetate

出典と根拠

ORDレコード
ord-450e4f1abcb741528cf798f1cb8baa32
出典データセット
uspto-grants-2010_06
特許番号
US07737160B2

関連ノート

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