trans-4-Decen-1-al → HCID 86702786, compound
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].[Li][CH2:34]CCC.[CH:38](=O)[CH2:39][CH2:40]/[CH:41]=[CH:42]/[CH2:43][CH2:44][CH2:45][CH2:46]C>>[CH3:34][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][CH2:38][CH2:39]/[CH:40]=[CH:41]/[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]Participants
4
Conditions
- Temperature
- 25 °C
Procedure
Starting from (1-(2-naphthyl)ethyltriphenylphosphonium bromide (4.50 g, 9.05 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 5.7 mL, 9.05 mmol, 1.0 equiv.) and (E)-dec-4-enal (2.09 g, 13.6 mmol, 1.5 equiv.), and after stirring the mixture at 25° C. for 3 h, 1.16 g (44%) of the title compound as a light yellow oil was obtained after purification by flash chromatography on SiO2 (cyclohexane).
Sources & evidence
- ORD record
- ord-897723e5a3fa4f4299808f910217a686
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193935B2
Reaction notes
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