5-Hydroxy-2-tetralone → 1,2,3,4-Tetrahydro-5-[2,3-epoxy-propoxy]-2-naphthol
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[CH2:7]2.[C:13]1(=[O:23])C2C(=CC=CC=2)C=[CH:15][CH2:14]1.C1(O)C2CCC(O)CC=2C=CC=1>>[O:23]1[CH2:13][CH:14]1[CH2:15][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([OH:12])[CH2:7]2Participants
Procedure
Employing the procedure of Example 3 a, 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 3 b to the corresponding 5-hydroxy-3,4-dihydro-2(1H)-naphthalenone shown in the middle column of Table II; employing the procedure of Example 3 c the naphthalenone is converted to the corresponding 5,6,7,8-tetrahydro-1,6-naphthalenediol which is reacted with an epoxide of the structure ##EQU13## 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 ##EQU14## 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-d4200412419642b3ad73963a3a43e8ab
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03935267
Reaction notes
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