3-Methoxybenzoic Acid → HCID 10964594, compound

HRID 234245Notes

Reaction equation

HRID 234245 reaction equation
[C:1]([OH:11])(=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8]C)[CH:3]=1.[Li]>N>[O:8]=[C:4]1[CH2:3][CH:2]([C:1]([OH:11])=[O:10])[CH:7]=[CH:6][CH2:5]1

Participants

4

Reactant 2

HCID 114613-Methoxybenzoic AcidHCID 3028194Lithium

Product 1

HCID 10964594HCID 10964594, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To synthesize methyl cis-3,5-dihydroxy-5-(trimethylsilylethynyl)cyclohex-1-ene-1-carboxylate, m-anisic acid is subjected to the Birch reduction with lithium in ammonia to produce 5-oxocyclohex-2-ene-1-carboxylic acid, followed by methylation of thus-produced cyclohex-2-ene-1-carboxylic acid to methyl 5-oxocyclohex-2-ene-1-carboxylate with diazomethane, trimethylsilyl-ethynylation of thus-produced cyclohex-2-ene-1-carboxylate with cerium dichloride trimethylsilylacetylene to produce methyl cis-5-hydroxy-5-(trimethylsilylethynyl)cyclohex-2-ene-1-carboxylate, conversion to an epoxide and opening of the resulting epoxide ring to produce the cis-3,5-dihydroxy compound.

Sources & evidence

ORD record
ord-b14bae74757c449790239e2a75d794ba
Source dataset
uspto-grants-1997_01
Patent number
US05594158

Reaction notes

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