Benzyltriphenylphosphonium bromide → Ethyl 3-(2-Phenylethenyl)indole-2-carboxylate

HRID 982033노트

반응식

HRID 982033 반응식
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=O.[Br-].[CH:18]1([CH2:24][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>>[C:18]1([CH:24]=[CH:1][C:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

4

반응물 3

HCID 2734970Benzyltriphenylphosphonium bromideHCID 5107764ethyl 3-formyl-1H-indole-2-carboxylateHCID 20068889(Cyclohexylmethyl)triphenylphosphonium bromide

생성물 1

HCID 53837799Ethyl 3-(2-Phenylethenyl)indole-2-carboxylate수율 73%

실험 절차

Using the procedure of Example 121 but replacing the resultant compound of Example 98 with the resultant compound of Example 97 and replacing the resultant compound of Example 120 with benzyltriphenylphosphonium bromide gave the desired compound in 73% yield after silica gel chromatography using 4:1 hexane/ethyl acetate. 1H NMR (CDCl3) δ 1.49 (t,J=7 Hz,3H), 4.48 (q,J=7 Hz,2H), 7.2-7.3 (m,2H), 7.35-7.45 (m,5H), 7.60 (br d,J=8 Hz,1H), 8.07 (d,J=16 Hz,1H), 8.16 (d,J=8 Hz,1H), 8.88 (br,1H). Mass spectrum: (M+H)+ =292.

출처 및 근거

ORD 기록
ord-9fc8fd91084e422fa11a57f3d61f1d82
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04994477

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