Ammonium Chloride → 8,8-Di-pyridin-2-yl-oct-7-enoic acid ethyl ester
Reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Br-].[CH2:12]([O:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:16])[CH3:13].[N:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[C:48]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][N:51]=1)=O.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH2:12]([O:14][C:15](=[O:16])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[C:48]([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][N:42]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][N:51]=1)[CH3:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
NaHMDS (10.01 mL, 10.01 mmol) as a solution in THF was added to (6-ethoxycarbonyl-hexyl)-triphenyl-phosphonium bromide I (10.54 mmol) in THF (40 mL) at −78° C. under Ar(g). After 30 min, di-pyridin-2-yl-methanone (1437 g, 7.81 mmol) in THF (5 mL) was added; the reaction was stirred for 2 h, and was then allowed to warm to rt. After 17 h, saturated aqueous NH4Cl (250 mL) and EtOAc (150 mL) were added; the phases were separated, and the aqueous phase was extracted with EtOAc (2×100 mL). The organic phases were combined, dried over MgSO4, filtered, and then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:0.5 to 100:2) to furnish II as a pale brown oil (990 mg, 40%).
Workup
- waitAfter 17 h
- customthe phases were separated
- extractionthe aqueous phase was extracted with EtOAc (2×100 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
- washeluting with CH2Cl2/MeOH (100:0.5 to 100:2)
Sources & evidence
- ORD record
- ord-8bcbf11b58d64e4ea778d6fa666c0541
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748458B2
Reaction notes
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