1,3,3-Trimethyl-2-methyleneindoline → HCID 15868837, 화합물

HRID 54602

반응식

HRID 54602 반응식
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([OH:17])[CH:8]=2)[CH2:3][CH2:2]1.[CH3:18][N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH3:29])([CH3:28])[C:20]1=[CH2:30].[CH2:31](OC(OCC)OCC)C>C(OCC)C>[CH3:18][N:19]1[C:20]2([O:17][C:9]3[CH:8]=[C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[C:16]4[C:11]([C:10]=3[CH:31]=[CH:30]2)=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:21]([CH3:28])([CH3:29])[C:22]2[C:27]1=[CH:26][CH:25]=[CH:24][CH:23]=2

참가 물질

5

반응물 3

HCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 31214Ethyl orthoformateHCID 109880424-Morpholino-2-naphthol

생성물 1

HCID 15868837HCID 15868837, 화합물수율 34%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A mixture of 4-morpholino-2-naphthol (0.47 g;0.002 mol), prepared as in 2(b) above, 1,3,3-trimethyl-2-methyleneindole (0.8 g;0.0022 mol) and triethylorthoformate (10.0 ml) was stirred under nitrogen and heated to reflux for 18 hrs. The resulting purple solution was cooled and evaporated to remove the excess triethylorthoformate and the residue flash chromatographed over silica (40% diethyl ether in hexane) to yield an orange gum (0.28 g; yield 34%). Trituration of the gum with diethyl ether afforded the 1,3,3-trimethyl-6'-morpholinospiro [indoline-2,3'-[3H]-naphtho[2,1-b]pyran having the structure shown below as a pale brown solid, m.pt 191°-194° C. ##STR20##

후처리

  1. temperatureheated
  2. temperatureto reflux for 18 hrs
  3. temperatureThe resulting purple solution was cooled
  4. customevaporated
  5. customto remove the excess triethylorthoformate
  6. customthe residue flash chromatographed over silica (40% diethyl ether in hexane)
  7. customto yield an orange gum (0.28 g; yield 34%)

출처 및 근거

ORD 기록
ord-65b5dd14fecf47bd973f6544bcddcf9c
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623005

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