3,4-dihydro-2H-pyran → 2-(5-Bromopentyloxy)tetrahydro-2H-pyran

HRID 471321

反応式

HRID 471321 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:25]1[CH:30]=[CH:29][CH2:28][CH2:27][CH2:26]1>C(Cl)Cl.CCOCC>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][O:25]1

参加物

6

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 1187091-Pentanol, 5-bromo-HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

生成物 1

HCID 27869332-(5-Bromopentyloxy)tetrahydro-2H-pyran

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-bromopentanol (10 g) in DCM (150 mL) was added pyridinium p-toluenesulfonate (1.5 g) followed by 3,4-dihydro-2H-pyran (8.1 mL) and the reaction mixture was stirred at room temperature under nitrogen for 21 hours. The solution was diluted with ether then washed with diluted brine (1:1 brine:water, 140 mL) before the organics were dried over sodium sulfate, filtered and evaporated. Purification was by silica gel chromatography eluting with 0 to 50% ethyl acetate in cyclohexane to afford the subtitled compound as a colourless liquid. Yield 14.14 g.

後処理

  1. washthen washed with diluted brine (1:1 brine:water, 140 mL) before the
  2. dry with materialorganics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customPurification
  6. washeluting with 0 to 50% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-6a57973373d740f98d5cad8b22a4f64f
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

関連ノート

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