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

HRID 982033ノート

反応式

HRID 982033 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

出典と根拠

ORDレコード
ord-9fc8fd91084e422fa11a57f3d61f1d82
出典データセット
uspto-grants-1991_02
特許番号
US04994477

反応ノート

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