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

HRID 437043

反応式

HRID 437043 の反応式
[C:1]1([OH:11])[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:20])C=1.C(OCC)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O1CCCC1>[O:20]1[CH:8]2[CH:7]1[CH2:6][C:5]1[CH:4]=[CH:3][CH:2]=[C:1]([OH:11])[C:10]=1[CH2:9]2

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 974665,8-Dihydro-1-naphthol2 回HCID 516892Sodium Bicarbonate

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Alternatively, the 2,3-trans-1,2,3,4-tetrahydro-5-[2-hydroxy-3-(alkylamino)propoxy]-2,3-naphthalenediol of formula II can be prepared from a 5,8-dihydro-1-naphthol of formula IX 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 a 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol having the formula ##STR17## A 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol of formula XVI in tetrahydrofuran can be reacted with aqueous perchloric acid at a temperature within the range of from about 0° to about 60° C., to form a trans-5,6,7,8-tetrahydro-1,6,7-naphthalenetriol or formula XI which can be converted to the corresponding 2,3-trans-1,2,3,4-tetrahydro-5-[2,3-(epoxy)propoxy]-2,3-naphthanediol of formula XII, which in turn can be converted to the corresponding 2,3-trans-1,2,3,4-tetrahydro-5-[2-hydroxy-3-(alkylamino)propoxy]-2,3-naphthalenediol of formula II using the procedures described above.

後処理

  1. additionmixing the resulting slurry

出典と根拠

ORDレコード
ord-8d8cea1e2f3a460a8df540716fddd2ab
出典データセット
uspto-grants-1977_06
特許番号
US04029676

関連ノート

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