Sodium Methoxide → Methyl 5-[1-(3-iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yloxymethyl)-vinyl]-3-thiophenecarboxylate

HRID 1075626Notes

Reaction equation

HRID 1075626 reaction equation
C[O-].[Na+].[I:4][C:5]1[C:6]([O:19][CH2:20][C:21]([C:23]2[S:27][CH:26]=[C:25]([C:28]([O:30][CH3:31])=[O:29])[CH:24]=2)=O)=[CH:7][C:8]2[C:9]([CH3:18])([CH3:17])[CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[C:13]=2[CH:14]=1.[Br-].[CH3:33]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CO.C1COCC1>[I:4][C:5]1[C:6]([O:19][CH2:20][C:21]([C:23]2[S:27][CH:26]=[C:25]([C:28]([O:30][CH3:31])=[O:29])[CH:24]=2)=[CH2:33])=[CH:7][C:8]2[C:9]([CH3:17])([CH3:18])[CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[C:13]=2[CH:14]=1

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 67581914Methyl 5-[(3-iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)-acetyl]-3-thiophenecarboxylateHCID 178503020HCID 178503020, compound

Product 1

HCID 67582983Methyl 5-[1-(3-iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yloxymethyl)-vinyl]-3-thiophenecarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 30% solution of sodium methoxide in methanol (1.68 ml) was added over 8 hours to a mixture of methyl 5-[(3-iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-acetyl]-3-thiophenecarboxylate (4.1 g, 8 mmol) and methyltriphenylphosphine bromide (3.8 g, 10.8 mmol) in THF (50 ml).

Sources & evidence

ORD record
ord-12175c8616ff4974bbfe474114097281
Source dataset
uspto-grants-1999_05
Patent number
US05905088

Reaction notes

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