1-Tetralone → HCID 14072855, compound

HRID 2291391Notes

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-d048a83cc7884a5fa2000fab4285e6b5
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04795819

Reaction notes

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