1,2-Dichloroethane → HCID 59294727, compound
Reaction equation
[CH2:1]([CH:21](CCC(CCCC(CCCC(CCCC(C)C)C)C)C)[OH:22])[CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])[CH3:4].Cl.CN(C)CCCC(O)=O.C(Cl)CCl.C(N(C(C)C)CC)(C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH2:1]([CH2:21][OH:22])[CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])[CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of diphytanyl methanol (6.4 g, 10.3 mmol) and 4-(dimethylamino) butyric acid hydrochloride (2.25 g, 13.4 mmol) in anhydrous dichloromethane (60 mL) under nitrogen at room temperature was added EDC (2.77 g, 18.0 mmol), diisopropylethylamine (5.4 mL, 31.0 mmol), and 4-dimethylaminopyridine (45 mg, 0.37 mmol). After 16 hours the reaction mixture was diluted with dichloromethane (75 mL). The organic layer was washed with saturated NaHCO3, water, and brine, and then dried on MgSO4, filtered, and concentrated. The resulting yellow oil was purified by column chromatography (column 10″L×2″W; eluted with a gradient of 100% hexanes→10%→50% ethyl acetate in hexanes) to afford the product as a pale yellow oil (3.53 g, 49%) with recovery of some phytanyl methanol (2.81 g, 44%).
Workup
- washThe organic layer was washed with saturated NaHCO3, water, and brine
- customdried on MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe resulting yellow oil was purified by column chromatography (column 10″L×
- washeluted with a gradient of 100% hexanes
Sources & evidence
- ORD record
- ord-1ed799a2c35548d097135e60f805649e
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865675B2
Reaction notes
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