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

HRID 17106

反応式

HRID 17106 の反応式
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1>ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][O:6][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1

参加物

5

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 423003-Iodobenzyl alcohol

生成物 1

HCID 601336982-(3-Iodo-benzyloxy)-tetrahydro-pyran収率 103.6%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 6344Dichloromethane溶媒

実験手順

para-Toluenesulfonic acid (100 mg, cat.) was added in one portion to a cooled solution (0 C) of 3-iodobenzyl alcohol (4.71 g, 0.02 mol) and dihydropyran (1.86 g, 0.022 mol) in dichloromethane (50 mL) under a nitrogen atmosphere. The cooling bath was removed and the reaction mixture was allowed to warm to room temperature over 1 hr. Diethyl ether (100 mL) was then added followed by saturated sodium hydrogen carbonate solution (100 mL). The organic layer was separated, dried (MgSO4) and evaporated in vacuo to yield the crude product (6.59 g) A332.1, which was used immediately without further purification. HPLC YMC S-5 4.6×33 mm (2 min grad): retention time 2.16 min, no M+H+ observed.

後処理

  1. customThe cooling bath was removed
  2. additionDiethyl ether (100 mL) was then added
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-13b29cc03d364b6f9c3b6efe538009bf
出典データセット
uspto-grants-2010_06
特許番号
US07737279B2

関連ノート

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