1-Tetralone → HCID 14072855, compound

HRID 1534049Notes

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-7f4a5b0018984fe5af9643bff18531ce
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05086182

Reaction notes

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