5,6,7,8-Tetrahydronaphthalene-1,6-diol → 1,2,3,4-Tetrahydro-5-[2,3-epoxy-propoxy]-2-naphthol
Reaction equation
[C:1]1(=[O:11])C2C(=CC=CC=2)C=[CH:3][CH2:2]1.[C:12]1([OH:23])[C:21]2[CH2:20][CH2:19][CH:18]([OH:22])[CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1>>[O:11]1[CH2:1][CH:2]1[CH2:3][O:23][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[CH2:20][CH2:19][CH:18]([OH:22])[CH2:17]2Participants
Procedure
Employing the procedure of Example 3a, but substituting a 6-alkoxy-1-tetralone as shown in the left hand (first) column of Table II for 6-methoxy-1-tetralone, a 6-alkoxy-1-naphthol is produced, which is converted as per Example 3b to the corresponding 5-hydroxy-3,4-dihydro-2(1H)-naphthalenenone shown in the middle column of Table II; employing the procedure of Example 3c the naphthalenone is converted to the corresponding 5,6,7,8-tetrahydro-1,6-naphthalenediol which is reacted with an epoxide of the structure ##STR52## in accordance with the procedure of Example 3d to form the corresponding 1,2,3,4-tetrahydro-5-[2,3-epoxy-propoxy]-2-naphthol which is reacted with an amine of the structure ##STR53## in accordance with the procedure of Example 3e to form the corresponding 1,2,3,4-tetrahydro-5-[2-hydroxy-3-(R1, R2 -substituted amino)propoxy]-2-naphthol (formula I) as shown in the right hand (third) column of Table II.
Sources & evidence
- ORD record
- ord-1312e13fe4f748ff8ac8b0d0e1bbd214
- Source dataset
- uspto-grants-1979_05
- Patent number
- US04156789
Reaction notes
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