(R,R,R)-2-allyl-3-(3-hydroxy-3,7,11,15-tetramethyl-hexadecyl)-5-methyl-[1,4]benzoquinone → (R,R,R)-3-(3-hydroxy-3,7,11,15-tetramethyl-hexadecyl)-5-methyl-2-propyl-benzene-1,4-diol
Reaction equation
[CH2:1]([C:4]1[C:5](=[O:33])[CH:6]=[C:7]([CH3:32])[C:8](=[O:31])[C:9]=1[CH2:10][CH2:11][C@@:12]([OH:30])([CH3:29])[CH2:13][CH2:14][CH2:15][C@H:16]([CH3:28])[CH2:17][CH2:18][CH2:19][C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:2]=[CH2:3]>O=[Pt]=O.CCOC(C)=O>[OH:30][C@:12]([CH3:29])([CH2:13][CH2:14][CH2:15][C@H:16]([CH3:28])[CH2:17][CH2:18][CH2:19][C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11][CH2:10][C:9]1[C:4]([CH2:1][CH2:2][CH3:3])=[C:5]([OH:33])[CH:6]=[C:7]([CH3:32])[C:8]=1[OH:31]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
(R,R,R)-2-allyl-3-(3-hydroxy-3,7,11,15-tetramethyl-hexadecyl)-5-methyl-[1,4]benzoquinone (Ex-1E-4) (115 mg, 0.25 mmol) was hydrogenated using PtO2 (6 mg) at 50 psi for 3 h in a solution of EtOAc (7 mL). The suspension was filtered through silica, which was rinsed with EtOAc (40 mL). The solution was concentrated by rotary evaporation to yield (R,R,R)-3-(3-hydroxy-3,7,11,15-tetramethyl-hexadecyl)-5-methyl-2-propyl-benzene-1,4-diol (Ex-1E-5) as a clear, colorless oil (110 mg, 96%), which was carried on to the next step without further purification.
Workup
- customfor 3 h
- filtrationThe suspension was filtered through silica, which
- washwas rinsed with EtOAc (40 mL)
- concentrationThe solution was concentrated by rotary evaporation
Sources & evidence
- ORD record
- ord-2835ecefb98a4d338adabe42bb6cc557
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447006B2
Reaction notes
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