Acetone → HCID 58771184, compound

HRID 63811

Reaction equation

HRID 63811 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH2:6][CH2:7][C@:8]([CH2:14][CH2:15][CH2:16][C@@H:17]([CH2:19][CH2:20][CH2:21][C@@H:22]([CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH3:23])[CH3:18])([CH3:13])[O:9]2)=[CH:4][C:3]=1[OH:30].C([O-])([O-])=O.[K+].[K+].[CH2:37](Br)[CH:38]=[CH2:39].CC(C)=O>O.CCOC(C)=O>[CH2:39]([O:30][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:12])[C:2]=1[CH3:1])[O:9][C@:8]([CH3:13])([CH2:14][CH2:15][CH2:16][C@H:17]([CH3:18])[CH2:19][CH2:20][CH2:21][C@H:22]([CH3:23])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:7][CH2:6]2)[CH:38]=[CH2:37]

Participants

7

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 92729(+)-gamma-Tocopherol

Product 1

HCID 58771184HCID 58771184, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

(+)-γ-tocopherol (Ex-1D-1) (300 mg, 0.72 mmol), K2CO3 (199 mg, 1.44 mmol), allyl bromide (182 μL, 1.44 mmol) and acetone (8 mL) were charged to a 50 mL RBF. The reaction was heated to reflux for 20 h after which time it was deemed complete by TLC (1:5 EtOAc:Hept). The reaction was diluted with water (10 mL). The aqueous layer was separated and washed with DCM (3×10 mL). The combined DCM layers were dried over Na2SO4, filtered and concentrated by rotary evaporation to yield a pale yellow oil. The oil was flashed through a silica plug (1:1: DCM:Heptane). After concentration of the eluent, (R,R,R)-6-allyloxy-2,7,8-trimethyl-2-(4,8,12-trimethyl-tridecyl)-chroman (Ex-1D-2) was obtained as a clear, colorless oil (334 mg, >100%), which was used without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 20 h after which time it
  3. customThe aqueous layer was separated
  4. washwashed with DCM (3×10 mL)
  5. dry with materialThe combined DCM layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customto yield a pale yellow oil

Sources & evidence

ORD record
ord-5e22e8559f554351a02c73537ddee332
Source dataset
uspto-grants-2016_09
Patent number
US09447006B2

Linked notes

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