1,2-Dichloroethane → HCID 59294727, compound

HRID 1478960Notes

Reaction equation

HRID 1478960 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

7

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 126916404-(Dimethylamino)butyric acid hydrochlorideHCID 58205088HCID 58205088, compound

Product 1

HCID 59294727HCID 59294727, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

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

  1. washThe organic layer was washed with saturated NaHCO3, water, and brine
  2. customdried on MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting yellow oil was purified by column chromatography (column 10″L×
  6. washeluted with a gradient of 100% hexanes

Sources & evidence

ORD record
ord-7d741c7c7ae346dd821a0cb9c65b7c57
Source dataset
uspto-grants-2016_08
Patent number
US09404127B2

Reaction notes

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