p-Toluenesulfonic acid → 3-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile

HRID 1161110ノート

反応式

HRID 1161110 の反応式
C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18].[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C(=O)(O)[O-].[Na+]>ClCCl>[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18]

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 27346773-(Hydroxymethyl)benzonitrile

生成物 1

HCID 219279093-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile収率 61%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Add p-toluene sulphonic acid (2.11 g, 12.2 mmol) to a solution of 3-hydroxymethyl-benzonitrile (16.30 g, 122.4 mmol) and 3,4-dihydro-2H-pyran (51.5 g, 612 mmol) in dichloromethane (500 ml) and stir. After 90 minutes, pour reaction into saturated sodium bicarbonate, remove organics, dry with sodium sulfate, filter and concentrate to give a dark brown oil. Purify the residue by flash chromatography eluting with a gradient of 10-15% ethyl acetate:hexanes to yield the title product as a clear oil (16.20 g, 61%): 1H NMR (CDCl3) δ 1.53-1.91 (m, 6H), 3.56 (m, 1H), 3.88 (m, 1H), 4.53 (d, 1H), 4.72 (t, 1H), 4.81 (d, 1H), 7.45 (t, 1H), 7.58 (m, 2H), 7.69 (s, 1H)

後処理

  1. additionpour
  2. customremove organics
  3. dry with materialdry with sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto give a dark brown oil
  7. customPurify the residue by flash chromatography
  8. washeluting with a gradient of 10-15% ethyl acetate

出典と根拠

ORDレコード
ord-1d4edb6558d94221a674081e706cc9dc
出典データセット
uspto-grants-2010_10
特許番号
US07816523B2

反応ノート

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