Ethyl bromoacetate → (+/-) ethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-8-(carbethoxymethyl) naphthalen-2-yl)ethenyl]benzoate

HRID 1289285

반응식

HRID 1289285 반응식
C1C2C(CC=CC=2)CCC1=O.C1C2C(=CC=CC=2)CCC1.[CH3:22][C:23]1([CH3:47])[CH2:32][CH2:31][C:30](=[O:33])[C:29]2[CH:28]=[C:27](/[CH:34]=[CH:35]/[C:36]3[CH:46]=[CH:45][C:39]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:38][CH:37]=3)[CH:26]=[CH:25][C:24]1=2.Br[CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51]>[Zn]>[CH3:47][C:23]1([CH3:22])[CH2:32][CH2:31][C:30]([OH:33])([CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])[C:29]2[CH:28]=[C:27](/[CH:34]=[CH:35]/[C:36]3[CH:37]=[CH:38][C:39]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:45][CH:46]=3)[CH:26]=[CH:25][C:24]1=2

참가 물질

6

반응물 4

HCID 7748Ethyl bromoacetateHCID 8404TetralinHCID 12069038Ethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethenyl]-benzoate2회HCID 69540356Tetrahydronaphthalene-2-one

생성물 1

HCID 20605993(+/-) ethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-8-(carbethoxymethyl) naphthalen-2-yl)ethenyl]benzoate

시약·촉매·용매 1

HCID 23994Zinc촉매

실험 절차

Reaction Scheme 5 discloses another example for the preparation of compounds within the scope of Formula 3. In this example the substituent is introduced to replace the oxo function of tetrahydronaphthalene-2-one after the Z-Y(R2)-A-B group has already been coupled to the tetrahydronaphthalene nucleus. Thus, ethyl (E)-4-[2-(5,6-dihydro-5,5-dimethyl-naphthalen-8(7H)-one-2-yl)ethenyl]benzoate (Compound A2) is reacted with ethyl bromoacetate in the presence of zinc metal in a Reformatsky reaction to provide (+/-) ethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-8-(carbethoxymethyl)naphthalen-2-yl)ethenyl]benzoate (Compound A32). Compound A32 is itself within the scope of the present invention, within the scope of Formula 1. Compound A32 is dehydrated, as shown in the example by treatment with (methoxycarbonyl sulfamoyl)triethylammonium hydroxide (Burgess reagent) to yield a mixture of ethyl (E)-4-[2-(5,6-dihydro-5,5-dimethyl-8-(carbethoxymethyl)naphthalen-2-yl)ethenyl]benzoate (Compound A33a), and ethyl (E)-4-[2-(5,6-dihydro-5,5-dimethyl-8(7H)-anti (carbethoxymethylidenyl)-naphthalen-2-yl)ethenyl]benzoate (Compound A33b). Compound A33a is within the scope of Formula 6, and Compound A33b is within the scope of Formula 3. ##STR20##

후처리

  1. customReaction Scheme 5

출처 및 근거

ORD 기록
ord-19e950ac52554a1da8327e03b88548d2
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05747542

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