Methane, dichloromethoxy- → 7-Benzyloxy-benzo[b]thiophene-4-carbaldehyde

HRID 479231노트

반응식

HRID 479231 반응식
[CH2:1]([O:8][C:9]1[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][O:19]C(Cl)Cl>ClCCl>[CH2:1]([O:8][C:9]1[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[C:12]([CH:18]=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 21004Methane, dichloromethoxy-HCID 226475147-Benzyloxy-benzo[b]thiophene

생성물 1

HCID 226476117-Benzyloxy-benzo[b]thiophene-4-carbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In analogy to the procedure described in example 91 b], 7-benzyloxy-benzo[b]thiophene (prepared from benzo[b]thiophen-7-ol [J. Chem. Soc., Perkin Trans. 1 (1983), (12), 2973-7], benzylchloride, potassium carbonate in N,N-dimethylformamide at room temperature) was reacted with dichloromethyl methyl ether in dichloromethane at 0° C. to give 7-benzyloxy-benzo[b]thiophene-4-carbaldehyde. Treatment of 7-benzyloxy-benzo[b]thiophene-4-carbaldehyde with (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride and potassium carbonate in 2-propanol in analogy to the procedure described in example 93 a] gave 3-(7-benzyloxy-benzo[b]thiophen-4-yl)-2(Z,E)-ethoxy-acrylic acid ethyl ester. Reduction of 3-(7-benzyloxy-benzo[b]thiophen-4-yl)-2(Z,E)-ethoxy-acrylic acid ethyl ester with magnesium in THF/MeOH (1:1) at 50° C. in analogy to the procedure described in example 93 b] yielded [rac]-3-(7-benzyloxy-benzo[b]thiophen-4-yl)-2-ethoxy-propionic acid methyl ester, subsequent removal of the benzyl protective function with dimethyl sulfide and boron trifluoride diethyl etherate in dichlormethane at room temperature in analogy the procedure described in example 93 c] gave [rac]-2-ethoxy-3-(7-hydroxy-benzo[b]thiophen-4-yl)-propionic acid methyl ester as light yellow oil.

출처 및 근거

ORD 기록
ord-a864ddb51aba489eb983c4070cb0b58a
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642389B2

반응 노트

불러오는 중…