3,4-dihydro-2H-pyran → 2-(4-Pentynyloxy)tetrahydro-2H-pyran

HRID 715961ノート

反応式

HRID 715961 の反応式
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([OH:12])[CH2:8][CH2:9][C:10]#[CH:11].C(=O)(O)[O-].[Na+]>CC1C=CC(S(O)(=O)=O)=CC=1>[CH2:7]([O:12][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1)[CH2:8][CH2:9][C:10]#[CH:11]

参加物

5

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 793464-Pentyn-1-olHCID 516892Sodium Bicarbonate

生成物 1

HCID 3578162-(4-Pentynyloxy)tetrahydro-2H-pyran収率 77.2%

試薬・触媒・溶媒 1

HCID 6101p-Toluenesulfonic acid触媒

実験手順

3,4-Dihydro-2H-pyran (5.0 g) was added dropwise to an ice cooled mixture of 4-pentyn-1-ol (5.0 g) and 4-methylbenzenesulfonic acid (0.512 g). The resultant mixture was stirred at room temperature for 4 hours. Solid sodium bicarbonate (1.0 g) was added and the mixture was stirred for 10 minutes, then filtered and washed with diethyl ether. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give 2-(pent-4-ynyloxy)tetrahydropyran (7.72 g) as a clear oil.

後処理

  1. temperaturecooled
  2. filtrationfiltered
  3. washwashed with diethyl ether
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

出典と根拠

ORDレコード
ord-3562ee54fdb14a73bf66059033640eed
出典データセット
uspto-grants-2015_11
特許番号
US09187494B2

反応ノート

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