Water → HCID 11805970, compound

HRID 411883Notes

Reaction equation

HRID 411883 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[SH:19][CH2:20][C@:21]12[C:27]([CH3:29])([CH3:28])[C@H:24]([CH2:25][CH2:26]1)[CH2:23][C@@:22]2([C:31]#[C:32][Si](C)(C)C)[OH:30].O>O1CCCC1>[CH3:28][C:27]1([CH3:29])[C@@H:24]2[CH2:25][CH2:26][C@:21]31[C@:22]([OH:30])([CH2:23]2)[C:31](=[CH2:32])[S:19][CH2:20]3

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 11119569HCID 11119569, compound

Product 1

HCID 11805970HCID 11805970, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylammonium fluoride (0.5 mL of a 1.0M solution in tetrahydrofuran) was added to a solution of alcohol 2 (65 mg, 0.23 mmol) in tetrahydrofuran (5 mL) under nitrogen. After two hours water was added to the solution and the resulting mixture extracted with dichloromethane. The combined organic extracts were washed with brine and dried over MgSO4. After filtration and removal of the solvents under reduced pressure, chromatography with 5% ethyl acetate in petrol gave sulfide 3 (31 mg, 64%), [a]20D−90.5 (c 2.10 in CHCl3); umax (thin film)/cm−1 3483 (OH), 2942 (CH), 1701 (C═C), 1627 (C═C); dH (250 MHz; CDCl3) 0.97 (3H, s, CH3), 1.01-1.16 (1H, m), 1.27 (3H, s, CH3), 1.50-1.83 (4H, m), 1.96-2.10 (2H, m), 2.14 (1H, br s, OH), 2.52 (1H, d, J 9.0, CHHS), 3.22 (1H, d, J 9.0, CHHS), 4.93 (1H, d, J 1.0, ═CHH), 5.12 (1H, d, J 1.0, ═CHH); dC (63 MHz; CDCl3) 22.02 (CH3), 22.05 (CH3), 26.89 (CH2), 31.95 (CH2), 32.07 (CH2), 37.38 (CH2), 46.25 (C), 50.79 (CH), 61.68 (C), 93.20 (C), 101.39 (CH2), 151.81 (C); m/z (EI) 210 (M+, 30%), 108 (57), 95 (100), 81 (27), (Found; M+, 210.1085. C12H18OS requires 210.1078).

Workup

  1. extractionthe resulting mixture extracted with dichloromethane
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration and removal of the solvents under reduced pressure, chromatography with 5% ethyl acetate in petrol

Sources & evidence

ORD record
ord-012fde11b93b4d85b9430f1133f91d96
Source dataset
uspto-grants-2003_05
Patent number
US06559323B1

Reaction notes

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