2,3-Dihydroxynaphthalene → 1a,2,7,7a-Tetrahydronaphtho[2,3-b]oxiren-3-ol

HRID 263315

반응식

HRID 263315 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](O)[C:2]=1[OH:12].C1([OH:23])C2CC=CCC=2C=CC=1.ClC1C=CC=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C(OCC)C>[O:12]1[CH:2]2[CH:3]1[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([OH:23])[C:10]=1[CH2:1]2

참가 물질

7

반응물 4

HCID 70912,3-DihydroxynaphthaleneHCID 70297m-Chloroperbenzoic acidHCID 974665,8-Dihydro-1-naphthol2회HCID 516892Sodium Bicarbonate

생성물 1

HCID 124457371a,2,7,7a-Tetrahydronaphtho[2,3-b]oxiren-3-ol

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

실험 절차

Alternatively, the 2,3-trans-1,2,3,4-tetrahydro-5-[2-hydroxy-3-(substituted-amino)propoxy]-2,3-naphthalenediol isomer XXVII can be prepared from a 5,8-dihydro-1-naphthol of the structure ##STR34## prepared as described hereinbefore, by mixing a cooled solution (temperature less than about 30° C.) of 5,8-dihydro-1-naphthol in ethyl acetate with m-chloroperbenzoic acid and mixing the resulting slurry with a mixture of ethyl ether and aqueous sodium bicarbonate, to form 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol ##STR35## and reacting the 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol in tetrahydrofuran with aqueous perchloric acid at a temperature within the range of from about 0° to about 60° C., to form trans-5,6,7,8-tetrahydro-1,6,7-naphthalenetriol XXV which can be converted to the 2,3-trans-1,2,3,4-tetrahydro-5-[2,3-(epoxy)-propoxy]-2,3-naphthalenediol XXVI which in turn can be converted to the 2,3-trans-1,2,3,4-tetrahydro-5-[2-hydroxy-3-substituted amino)propoxy]-2,3-naphthalenediol XXVII in a manner similar to that described hereinbefore.

후처리

  1. customprepared
  2. additionmixing the resulting slurry

출처 및 근거

ORD 기록
ord-07f280a69a2944558d7a0fcb18fd2216
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04156789

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