1,3-Propanediol → HCID 59379101, compound

HRID 1670382Notes

Reaction equation

HRID 1670382 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][OH:6].[CH2:8](CS([O-])(=O)=O)[CH2:9][CH:10]([CH2:12][CH2:13][CH2:14][CH:15]([CH2:17][CH2:18][CH2:19][CH:20]([CH2:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH3:21])[CH3:16])[CH3:11]>>[CH2:8]([O:6][CH2:5][CH2:4][CH2:3][OH:7])[CH2:9][CH:10]([CH2:12][CH2:13][CH2:14][CH:15]([CH2:17][CH2:18][CH2:19][CH:20]([CH2:22][CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[CH3:21])[CH3:16])[CH3:11]

Participants

4

Reactant 3

HCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 59294723HCID 59294723, compound

Product 1

HCID 59379101HCID 59379101, compoundYield 87.6%

Conditions

Temperature
60 °C

Procedure

Sodium hydride was added carefully to a solution of 1,3-propanediol (7.6 g, 100 mmol) in anhydrous N,N-DMF (30 mL). Phytanylmethanesulfonate (1.5 g, 4 mmol) was added and the mixture was heated to 60° C. and stirred for 4 h. The reaction mixture was then poured into ice/H2O, extracted with dichloromethane, dried over MgSO4 and evaporated. The residue was purified by flash column chromatography using 20% ethyl acetate/hexanes to give 3-(phytanyloxy)propan-1-ol (1.25 g, 87% yield)

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-b346b27a439444e29555fb562373a56b
Source dataset
uspto-grants-2011_08
Patent number
US07994143B2

Reaction notes

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