Dodecanoyl chloride → HCID 9865002, compound

HRID 2399912Notes

Reaction equation

HRID 2399912 reaction equation
[OH:1][CH2:2][C:3]1[CH:7]([CH3:8])[O:6][C:5](=[O:9])[C:4]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16](Cl)(=[O:28])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C1COCC1>[C:16]([O:1][CH2:2][C:3]1[CH:7]([CH3:8])[O:6][C:5](=[O:9])[C:4]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:28])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 15295494HCID 15295494, compound2×

Product 1

HCID 9865002HCID 9865002, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxymethyl-5-methyl-3-phenyl-2(5H)-furanone (Compound 7), (73 mg, 0.36 mmol), lauroyl chloride (117 mg, 0.54 mmol), triethylamine (47 mg, 0.47 mmol) and dimethylaminopyridine (1 mg, 0.01 mmol) were stirred in anhydrous THF (2 mL) at ambient temperature under argon for 2 hours. The crude reaction mixture was concentrated, the organics were extracted into diethyl ether and solids were filtered off. The ether was removed by rotary evaporator and the resulting oil was purified by flash chromatography on silica to give the title compound.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. extractionthe organics were extracted into diethyl ether and solids
  4. filtrationwere filtered off
  5. customThe ether was removed by rotary evaporator
  6. customthe resulting oil was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-f6331677e6984201a1a4be3cf385bdea
Source dataset
uspto-grants-1995_09
Patent number
US05451686

Reaction notes

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