p-Toluenesulfonic acid → 1-Methyl-1,3,4,9-tetrahydro-6-(phenylmethoxy)pyrano[3,4-b]indole-1-aceticacid, ethyl ester

HRID 484249

反応式

HRID 484249 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]3[NH:15][CH:16]=[C:17]([CH2:18][CH2:19][OH:20])[C:11]=3[CH:10]=2)=[CH:3][CH:2]=1.[C:21]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:22][C:23]([CH3:25])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:25][C:23]1([CH2:22][C:21]([O:27][CH2:28][CH3:29])=[O:26])[C:16]2[NH:15][C:12]3[C:11]([C:17]=2[CH2:18][CH2:19][O:20]1)=[CH:10][C:9]([O:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[CH:14][CH:13]=3

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 8868Ethyl AcetoacetateHCID 7448495-Benzyloxy-3-(2-hydroxyethyl)indole

生成物 1

HCID 1317180291-Methyl-1,3,4,9-tetrahydro-6-(phenylmethoxy)pyrano[3,4-b]indole-1-aceticacid, ethyl ester収率 85.3%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture consisting of 5-benzyloxytryptophol (4.5 g, 0.017 mol), benzene (200 mL), ethyl acetoacetate (3.4 g, 0.026 mol) and p-toluenesulfonic acid (0.5 g) is refluxed for 2.5 hours using a Dean-stock trap to remove the water. The reaction mixture is cooled to room temperature and washed with 5% sodium bicarbonate, (1×200 mL), water (200 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated to give 8.0 g of crude product as a thick oil, which is flash chromatographed on silica gel using 20% ethyl acetate/hexane as an eluent to afford 5.5 g oil which solidifies upon standing, m.p. 96°-98° C.

後処理

  1. temperatureis refluxed for 2.5 hours
  2. customto remove the water
  3. washwashed with 5% sodium bicarbonate, (1×200 mL), water (200 mL) and brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 8.0 g of crude product as a thick oil, which
  8. customchromatographed on silica gel using 20% ethyl acetate/hexane as an eluent

出典と根拠

ORDレコード
ord-81281567c4c44990919e4c9f2a565b1f
出典データセット
uspto-grants-1993_07
特許番号
US05229516

関連ノート

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