1-Tetralone → HCID 14072855, compound

HRID 1085987Notes

Reaction equation

C1(=O)C2C(=CC=CC=2)CCC1.[CH2:12]1[O:24][C:23]2[CH:22]=[C:21]3[C:16]([C:17](=[O:40])[CH2:18][CH:19]([C:37]([OH:39])=[O:38])[CH:20]3[C:25]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=3)=[CH:15][C:14]=2[O:13]1.[BH4-].[Na+]>>[CH2:12]1[O:24][C:23]2[CH:22]=[C:21]3[C:16]([CH:17]([OH:40])[CH2:18][CH:19]([C:37]([OH:39])=[O:38])[CH:20]3[C:25]3[CH:26]=[C:27]([O:35][CH3:36])[C:28]([O:33][CH3:34])=[C:29]([O:31][CH3:32])[CH:30]=3)=[CH:15][C:14]=2[O:13]1

Participants

Reactant 3

HCID 107241-Tetralone

HCID 4311764Sodium borohydride

HCID 19894807HCID 19894807, compound

Product 1

HCID 14072855HCID 14072855, compound

Procedure

The tetralone VIb prepared in Example 2 was hydrolyzed according to the procedure described by W. S. Murphy and S. Wattanasin, J.C.S. Perkin I, 271 (1982), and the resulting 1,2,3,4-tetrahydro-6,7-methylenedioxy-4-oxo-1-(3,4,5-trimethoxyphenyl)naphthalene-2-carboxylic acid (VId) was treated with sodium borohydride according to the general procedure described by W. J. Gensler et al., J. Am. Chem. Soc., 82, 1714 (1960) to give the title compound as a crystalline solid; m.p. 191.5°-193° C. (reported m.p. 181.4°-182° C.).

Sources & evidence

ORD record: ord-937df29015e940e19599d6ee178be0b8
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05011948

Reaction notes

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