Trifluoroacetic acid → HCID 58264329, compound

HRID 1259005Notes

Reaction equation

HRID 1259005 reaction equation
C([O:4][CH2:5][CH:6]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38]/[CH:39]=[CH:40]\[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])C=C.FC(F)(F)C(O)=O>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:28]([O:27][CH:6]([CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:5][OH:4])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38]/[CH:39]=[CH:40]\[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58264321HCID 58264321, compound

Product 1

HCID 58264329HCID 58264329, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of (6Z,9Z)-18-(3-(allyloxy)-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propoxy)octadeca-6,9-diene (9.1 g, 14.3 mmol) in ethanol (100 ml) was added trifluoroacetic acid (15.0 mL) and tetrakis(triphenylphosphine)palladium(0) (1.65 g, 1.43 mmol). The solution was refluxed for 16 hours, cooled to room temperature and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (eluted with a gradient of 100% hexanes to 1:1 hexanes/DCM to 100% DCM) to afford 2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-ol as a colorless oil (6.1 g, 54%).

Workup

  1. temperatureThe solution was refluxed for 16 hours
  2. concentrationconcentrated in vacuo to dryness
  3. customThe residue was purified by column chromatography on silica gel 60 (
  4. washeluted with a gradient of 100% hexanes to 1:1 hexanes/DCM to 100% DCM)

Sources & evidence

ORD record
ord-cdd0f5ee404f4e30bc3c5ec041145060
Source dataset
uspto-grants-2013_06
Patent number
US08466122B2

Reaction notes

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