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

HRID 1717797노트

반응식

HRID 1717797 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 219279093-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile수율 61%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c9838b339b1f435a9ab7e5a28d4cf0f3
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803938B2

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