Potassium Carbonate → (+/-)-3-[2-(Benzyloxy)-3-tert-butylphenyl]propane-1,2-diol

HRID 2115923Notes

Reaction equation

HRID 2115923 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:11]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)C=C.O.[C:29]([OH:33])(C)(C)C>C(O)(C)(C)C.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].CC[C@H]1[C@@H]2C[C@H]([C@H](OC3C=CC(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@@H](CC)[C@@H](CC5)C4)=C4C(C5C(C(=O)C=34)=CC=CC=5)=O)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1>[CH2:21]([O:20][C:11]1[C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:7][CH:1]([OH:4])[CH2:29][OH:33])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 689642861-Allyl-2-(benzyloxy)-3-tert-butylbenzeneHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 68966426(+/-)-3-[2-(Benzyloxy)-3-tert-butylphenyl]propane-1,2-diolYield 92%

Reagents, catalysts & solvents 3

HCID 713113981,4-Bis((R)-((1S,2R,4S,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)anthracene-9,10-dioneCatalystHCID 178511488HCID 178511488, compoundCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of potassium ferricyanide (57.00 g, 0.173 mol), potassium carbonate (24.00 g, 0.174 mol), hydroquinine anthraquinone-1,4-diyl diether (0.495 g, 0.578 mmol), and potassium osmate dihydrate (0.043 g, 0.117 mmol) in water:tert-butyl alcohol (1:1, 600 mL) cooled to 0° C. was slowly added via an addition funnel a solution of 1-allyl-2-(benzyloxy)-3-tert-butylbenzene (16.2 g, 0.058 mol) in tert-butyl alcohol (50 mL) and the reaction mixture was allowed to stir at 0° C. for 12 h. The reaction mixture was quenched by the addition of sodium sulfite. The reaction mixture was diluted with water (500 mL) and ethyl acetate (500 mL). The aqueous phase was separated and extracted with ethyl acetate (2×200 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (400 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 3:2) gave 16.75 g (92%, 32% ee) of (±)-3-[2-(benzyloxy)-3-tert-butylphenyl]propane-1,2-diol as a white solid. mp 79-81° C.; Anal. calcd. for C20H26O3: C, 76.4; H, 8.33. Found: C, 76.39; H, 8.22.

Workup

  1. customThe reaction mixture was quenched by the addition of sodium sulfite
  2. additionThe reaction mixture was diluted with water (500 mL) and ethyl acetate (500 mL)
  3. customThe aqueous phase was separated
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. washThe combined organic extracts were washed with saturated aqueous sodium chloride (400 mL)
  6. dry with materialdried (magnesium sulfate)
  7. customthe solvent was removed in vacuo
  8. customto give a crude oil
  9. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 3:2)

Sources & evidence

ORD record
ord-bb00bd2dd2004bd5b2c01ba3024a51fd
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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