Tetrahydrofuran → 2-[(11E)-trideca-2.1 l-dien-2-yl]naphthalene
Reaction equation
[Br-].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:13].[CH:33](=O)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]/C.[CH2:45]1COCC1>>[CH3:45][C:12]([C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=1)=[CH:13][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]/[CH:35]=[CH:34]/[CH3:33]Participants
4
Procedure
Starting from (1-(2-naphthyl)ethyltriphenylphosphonium bromide (49.7 g, 100 mmol, 1.0 equiv.) in THF (400 mL), KtBuO (110 mL, 110 mmol, 1.1 equiv., 1M in THF) and (E)-undec-9-enal (16.8 g, 120 mmol, 1.2 equiv.) in THF (100 mL), 16.6 g (53%) of the title compound was obtained after purification by flash chromatography on SiO2 (hexane) as a light yellow oil.
Sources & evidence
- ORD record
- ord-6a88a498add74b1ba6e52a23cf6efc8e
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193935B2
Reaction notes
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