Water → HCID 59627881, compound

HRID 1367679Notes

Reaction equation

HRID 1367679 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][C@@H:11]([CH:13]=[CH2:14])[C@H:10]([O:15][Si](CC)(CC)CC)[C:9]=2[CH3:23])=[N:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>C1COCC1>[CH3:23][C:9]1[C@@H:10]([OH:15])[C@H:11]([CH:13]=[CH2:14])[CH2:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 67267704HCID 67267704, compound

Product 1

HCID 59627881HCID 59627881, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 95 (50 mg, 0.152 mmol) in THF (1 ml) at 0° C. was added tetrabutylammonium fluoride (0.152 ml of 1 M solution in THF, 0.152 mmol) dropwise. The reaction mixture was stirred at 0° C. for 30 min and water (1 ml) and ethyl acetate (2 ml) were added. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×2 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash column chromatography on silica (16-50% EtOAc/hexanes) afforded pure alcohol 96 (28 mg, 83%) as a white solid: [α]22D=−26.0 (c 0.3, CHCl3); TLC Rf=0.25 (silica gel, 50% EtOAc/hexanes); 1H NMR (600 MHz, CDCl3) δ 8.43 (s, 1H), 7.47-7.44 (dd, 1H, 3J=1.8 Hz, 2J=7.8 Hz), 7.19-7.17 (d, 1H, 3J==7.8 Hz), 6.0-5.95 (m, 1H), 5.12-5.17 (d, 1H, 3J=16.8 Hz), 5.09-5.06 (d, 1H, 3J=10.2 Hz), 4.48 (s, 1H), 2.96-2.91 (m, 1H), 2.69-2.60 (m, 2H), 2.32 (s, 3H), 2.03 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 153.62, 149.90, 140.25, 139.41, 136.65, 135.55, 131.19, 122.32, 115.43, 86.42, 52.26, 38.52, 18.49, 13.17; HRMS calcd for C14H17NO+Na+ 238.1208; found 238.1191 [M+Na+].

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×2 ml)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by flash column chromatography on silica (16-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-da7fc73a63b14964a01ef4bee62f09fe
Source dataset
uspto-grants-2011_02
Patent number
US07893268B2

Reaction notes

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