HCID 14478570, compound → alpha-Tocopherol

HRID 1199327Notes

Reaction equation

HRID 1199327 reaction equation
[CH3:1][C:2]1([C:23]#[C:24][CH2:25][CH:26]([CH3:38])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:37])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:7][CH2:6][C:5]2[C:8]([CH3:22])=[C:9]([O:14]CC3C=CC=CC=3)[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]([CH2:23][CH2:24][CH2:25][C@@H:26]([CH2:27][CH2:28][CH2:29][C@@H:30]([CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH3:37])[CH3:38])([CH3:1])[O:3]2)=[C:8]([CH3:22])[C:9]=1[OH:14]

Participants

5

Reactant 1

HCID 14478570HCID 14478570, 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-(phenylmethoxy)-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-5b8ee4c2a5c24fbbbfe5ec999219bc7a
Source dataset
uspto-grants-1990_02
Patent number
US04900476

Reaction notes

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