(Triphenylphosphoranylidene)acetaldehyde → 1,8-Diazabicyclo(5.4.0)undec-7-ene

HRID 1602111

反応式

HRID 1602111 の反応式
ClC1C=C2C(=CC=1)[NH:7]C(C=O)=C2.C(C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O.[Cl:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[NH:41][C:40](/[CH:45]=[CH:46]/[CH:47]=[O:48])=[CH:39]2>>[Cl:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[NH:41][C:40](/[CH:45]=[CH:46]/[CH:47]=[O:48])=[CH:39]2.[CH2:36]1[CH2:44][CH2:43][N:7]2[C:42](=[N:41][CH2:40][CH2:45][CH2:46]2)[CH2:38][CH2:37]1

参加物

5

反応物 3

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 122033185-Chloro-1H-indole-2-carbaldehydeHCID 196104093-(5-chloro-1H-indol-2-yl)prop-2-enal

生成物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 196104093-(5-chloro-1H-indol-2-yl)prop-2-enal

実験手順

5-Chloroindole-2-carboxaldehyde was prepared starting from ethyl 5-chloroindole-2-carboxylate (7.4 g, 33 mmol) according to the procedure of Preparation 1, obtaining 2 g of a yellow solid, m.p.=208-209° C. The aldehyde (1.2 g, 6.7 mmol) was transformed in (E)-3-(5-chloro-2-indolyl)-2-propenaldehyde through the reaction with (formylmethylene)triphenylphosphorane (2 g, 6.7 mmol) following the procedure described in Preparation 2, obtaining 0.5 g of yellow powder, m.p.=207-209° C. (E)-3-(5-Chloro-2-indolyl)-2-propenaldehyde (0.5 g, 2.4 mmol) and DBU (0.75 ml, 5 mmol) were treated with methyl 2-methoxy-2-(triphenylphosphonium)acetate bromide (2.16 g, 5 mmol) according to the procedure of Example 1A to afford 250 mg (47%) of the title compound, m.p.=166-168° C.

後処理

  1. customdescribed in Preparation 2

出典と根拠

ORDレコード
ord-9a95198968204417a34fef68ff07b790
出典データセット
uspto-grants-1999_11
特許番号
US05981525

関連ノート

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