Methanol → 5-Bromo-2-[1-(3-iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yloxymethyl)vinyl]thiophene
Reaction equation
C[O-].[Na+].CO.[Br:6][C:7]1[S:11][C:10]([C:12](=O)[CH2:13][O:14][C:15]2[C:24]([I:25])=[CH:23][C:22]3[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:29])([CH3:28])[C:17]=3[CH:16]=2)=[CH:9][CH:8]=1.[Br-].[CH3:32]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[Br:6][C:7]1[S:11][C:10]([C:12]([CH2:13][O:14][C:15]2[C:24]([I:25])=[CH:23][C:22]3[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:29])[C:17]=3[CH:16]=2)=[CH2:32])=[CH:9][CH:8]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 30% sodium methoxide in methanol (1.65 ml, 8.66 mmol) was added over 8 hours to a mixture of 5-bromo-2-[(3-iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)acetyl]thiophene (4.3 g, 7.9 mmol) and methyltriphenylphosphine bromide (3.8 g, 10.7 mmol) in THF (45 ml). The mixture was stirred for 12 h at room temperature. The mixture was concentrated in a rotary evaporator under vacuum at 40° C. It was extracted with ethyl ether and washed with water. The organic phase was then dried over magnesium sulfate and concentrated in a rotary evaporator under vacuum at 40° C.
Workup
- concentrationThe mixture was concentrated in a rotary evaporator under vacuum at 40° C
- extractionIt was extracted with ethyl ether
- washwashed with water
- dry with materialThe organic phase was then dried over magnesium sulfate
- concentrationconcentrated in a rotary evaporator under vacuum at 40° C.
Sources & evidence
- ORD record
- ord-6c5c9b8423c7499190babbf1535f5e55
- Source dataset
- uspto-grants-1999_05
- Patent number
- US05905088
Reaction notes
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