Pyridine → 3,7,11,15-Tetramethyl-hexadecyl chloroformate

HRID 1910408Notes

Reaction equation

HRID 1910408 reaction equation
[CH2:1]([OH:21])[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:22][C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>ClCCl>[Cl:22][C:23]([O:21][CH2:1][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])=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 102459Dihydrophytol

Product 1

HCID 585385033,7,11,15-Tetramethyl-hexadecyl chloroformateYield 264.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phytanol (48.8 g, 163.5 mmol), and triphosgene (16.17 g, 54.66 mmol) were dissolve in 300 ml of dichloromethane, stirred and cooled on an ice bath. Anhydrous pyridine (12.93 g, 163.5 mmol) was added dropwise over a period of 1 hour. The reaction mixture was stirred for an additional 1 h at room temperature, and then quickly extracted with extra methylene chloride and ice water. The organic layer was pooled, dried over Na2SO4 and evaporated to dryness to yield 52.22 g (88.7%) of phytanyl chloroformate as yellow liquid. 1H NMR in CDCl3: δ0.83, 0.85, 0.86, 0.88, (4s, each 3H, CH3), 0.91 (d, 3H, J=6.0 Hz, CH3), 0.95-1.40 (m, 20H, CH2), 1.39-1.68 (m, 4H, CH), 1.68-1.88 (m, 1H, OH), 4.27-4.47 (m, 2H, CH2OH).

Workup

  1. temperaturecooled on an ice bath
  2. stirringThe reaction mixture was stirred for an additional 1 h at room temperature
  3. extractionquickly extracted with extra methylene chloride and ice water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-271bca6dcdf04dd1bf88d95f888c6518
Source dataset
uspto-grants-2013_12
Patent number
US08603999B2

Reaction notes

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