HCID 76456971, compound → alpha-Tocopherol

HRID 1199250Notes

Reaction equation

HRID 1199250 reaction equation
[CH3:1][C:2]1([C:22]#[C:23][CH2:24][CH:25]([CH3:37])[CH2:26][CH2:27][CH2:28][CH:29]([CH3:36])[CH2:30][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:7][CH2:6][C:5]2[C:8]([CH3:21])=[C:9]([O:14]CCCCCC)[C:10]([CH3:13])=[C:11]([CH3:12])[C:4]=2[O:3]1>[Ni].C(O)C.C(OCC)(=O)C>[CH3:13][C:10]1[C:11]([CH3:12])=[C:4]2[C:5]([CH2:6][CH2:7][C@:2]([CH2:22][CH2:23][CH2:24][C@@H:25]([CH2:26][CH2:27][CH2:28][C@@H:29]([CH2:30][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH3:36])[CH3:37])([CH3:1])[O:3]2)=[C:8]([CH3:21])[C:9]=1[OH:14]

Participants

5

Reactant 1

HCID 76456971HCID 76456971, compound

Product 1

HCID 14985alpha-TocopherolYield 101.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [2S-(4R*,8R*,)]-3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyl-1-tridecynyl)-6-(pentylmethoxy)-2H-1-benzopyran, (200 mg, 0.39 mmol) and 40 mg of Raney Nickel in 5 mL of ethanol and 5 mL of ethyl acetate was hydrogenated at 25° C. and atmospheric pressure for 6 h. Workup in the usual manner and purification of the crude product by chromatography on silica gel (eluent 1:5 ether-hexanes) gave 170 mg of (2R,4'R,8'R)-α-tocopherol as a pale yellow oil, identical in all aspects with a known sample.

Workup

  1. customwas hydrogenated at 25° C.
  2. customWorkup in the usual manner and purification of the crude product by chromatography on silica gel (eluent 1:5 ether-hexanes)

Sources & evidence

ORD record
ord-40b314fd017b47a7a5e8fa4d24afd77e
Source dataset
uspto-grants-1990_02
Patent number
US04898962

Reaction notes

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