3-(Benzenesulfonyl)-7-methoxy-2-benzofuran-1(3H)-one → HCID 20266223, compound

HRID 1719983Notes

Reaction equation

HRID 1719983 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[O:9][CH:8]2S(C1C=CC=CC=1)(=O)=O.CC(C)([O-])C.[Li+].[C:28]([CH:31]1[CH2:40][CH2:39][CH:38]2[CH:33]([CH2:34][CH:35]=[CH:36][C:37]2=[O:41])[CH2:32]1)(=[O:30])[CH3:29]>C1COCC1>[C:28]([C:31]1[CH:32]=[C:33]2[C:38]([C:37](=[O:41])[C:36]3[CH:10]([OH:12])[CH:11]4[C:7](=[C:8]([OH:9])[C:35]=3[CH2:34]2)[CH2:6][CH2:5][CH2:4][CH:3]4[O:2][CH3:1])=[CH:39][CH:40]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 109576723-(Benzenesulfonyl)-7-methoxy-2-benzofuran-1(3H)-oneHCID 13457043HCID 13457043, compoundHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

Product 1

HCID 20266223HCID 20266223, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Continuing with a synthesis utilizing the object compound (5) to produce the tetrahydronaphthacene dione intermediate, the anion of 7-methoxy-3-phenylsulfonyl-1(3H)-isobenzofuranone (6) as generated at -78° C. using lithium t-butoxide in THF and reacted with the hexahydronaphthalenone (5) to furnish 9-acetyl-5,12-dihydroxy-4-methoxy-6(11H)-hexahydronaphthacenone (7) in 95% yield. Conversion of (7) to 9-acetyl-6-hydroxy-4-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-dione (8) was achieved by heating (7) in dimethylforamide under oxygen at 45° C. for 18 hours.

Workup

  1. customas generated at -78° C.

Sources & evidence

ORD record
ord-3d8905cbc3e1472e900f3df40e651b1e
Source dataset
uspto-grants-1985_09
Patent number
US04543428

Reaction notes

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