Butanethiol → HCID 59949249, compound

HRID 1532877Notes

Reaction equation

HRID 1532877 reaction equation
[CH2:1]([SH:5])[CH2:2][CH2:3][CH3:4].[CH:6]1([CH2:12][C@H:13]2[CH2:15][O:14]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[H-].[Na+]>CN(C=O)C>[CH2:1]([S:5][CH2:15][C@@H:13]([OH:14])[CH2:12][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8012ButanethiolHCID 24758Sodium hydrideHCID 59949024HCID 59949024, compound

Product 1

HCID 59949249HCID 59949249, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Butanethiol (765 μL, 7.1 mmol), the product from Example 1308C (500 mg, 3.6 mmol) in DMF (3.0 mL), and NaH, 60% dispersion in mineral oil, (305 mg, 7.6 mmol) in DMF (40 mL) were allowed to react in a manner similar to that described in Example 1310A. The residue was chromatographed (silica gel; EtOAc/hexanes 1:40) to afford a clear oil (641 mg, 77%). 1H NMR (CDCl3, 300 MHz) δ0.80-1.00 (m, 2H), 0.92 (t, J=7 Hz, 3H), 1.08-1.34 (m, 4H), 1.37-1.75 (m, 10H), 1.81 (m, 1H), 2.42 (dd, J=9, 13.5 Hz, 1H), 2.53 (t, J=7 Hz, 2H), 2.72 (dd, J=3, 13.5 Hz, 1H), 3.76 (m, 1H); MS (CI/NH3) m/z: 231 (M+H)+.

Workup

  1. customto react in a manner similar to
  2. customThe residue was chromatographed (silica gel; EtOAc/hexanes 1:40)

Sources & evidence

ORD record
ord-f4814d931bc6469995ba24df050e894d
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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