Tetrahydrofuran → 3,5-Dimethoxy-4-(((2S,3S)-3-methyl-3-(4-methylpent-3-en-1-yl)oxiran-2-yl)methyl)phenol

HRID 633644Notes

Reaction equation

HRID 633644 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:40]=[C:41]([O:54][CH3:55])[C:42]=1[CH2:43][C@H:44]1[C@:46]([CH3:53])([CH2:47][CH2:48][CH:49]=[C:50]([CH3:52])[CH3:51])[O:45]1)[O:29][Si](C(C)C)(C(C)C)C(C)C.CCCCCC>CCOC(C)=O>[CH3:55][O:54][C:41]1[CH:40]=[C:28]([OH:29])[CH:27]=[C:26]([O:25][CH3:24])[C:42]=1[CH2:43][C@H:44]1[C@:46]([CH3:53])([CH2:47][CH2:48][CH:49]=[C:50]([CH3:52])[CH3:51])[O:45]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8058HexaneHCID 2724141Tetrabutylammonium FluorideHCID 90123972HCID 90123972, compound

Product 1

HCID 901238503,5-Dimethoxy-4-(((2S,3S)-3-methyl-3-(4-methylpent-3-en-1-yl)oxiran-2-yl)methyl)phenolYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tetrabutylammonium fluoride in THF (1 M, 9.0 mL, 9.01 mmol, 1.05 equiv.) was added to a THF (30 mL) solution of 5 (3.97 g, 8.58 mmol, 1 equiv.) in a 100-mL pear-shaped flask. After stirring for 30 min, the reaction was quenched with saturated aqueous NH4Cl and extracted once with hexane and twice with EtOAc. The organic extracts were combined, washed with brine, Na2SO4, filtered, and concentrated in vacuo to a slight yellow oil. Flash column chromatography (400 mL SiO2, 7:3 to 1:1 hexane:EtOAc) afforded 2.20 g (7.18 mmol, 84% yield) of 6 as a clear, colorless oil. TLC Rf 0.5 (1:1 hexane:EtOAc). 1H NMR (500 MHz; CDCl3): δ 6.06 (s, 2H), 5.11 (s, 1H), 4.99 (t, J=7.1 Hz, 1H), 3.76 (s, 6H), 2.97 (dd, J=13.5, 4.6 Hz, 1H), 2.91 (dd, J=7.3, 4.6 Hz, 1H), 2.69 (dd, J=13.5, 7.3 Hz, 1H), 2.07-1.95 (m, 2H), 1.63 (ddd, J=13.9, 9.1, 5.2 Hz, 1H), 1.59 (s, 3H), 1.54 (s, 3H), 1.38 (s, 3H), 1.37-1.33 (m, 1H). 13C NMR (125 MHz; CDCl3): δ 159.3, 156.4, 131.9, 123.8, 106.1, 92.1, 64.1, 62.6, 55.7, 39.1, 25.8, 24.1, 22.3, 17.7, 16.9. IR (NaCl, thin film, cm−1) 3368 (br), 2936, 2840, 1618, 1603, 1475, 1431, 1206, 1134, 999, 816.

Workup

  1. customthe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted once with hexane and twice with EtOAc
  3. washwashed with brine, Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a slight yellow oil

Sources & evidence

ORD record
ord-b8ecfbb995774ef19ab2686720c1f8a0
Source dataset
uspto-grants-2016_04
Patent number
US09321713B2

Reaction notes

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