Thiophenol → HCID 16074361, compound

HRID 1815122Notes

Reaction equation

HRID 1815122 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:15]([C:19]1([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[O:24][C:23](=[O:25])[CH:22](Cl)[C:21](=[O:27])[CH2:20]1)[CH2:16][C:17]#[CH:18]>CN(C=O)C>[CH2:15]([C:19]1([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[O:24][C:23](=[O:25])[CH:22]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:21](=[O:27])[CH2:20]1)[CH2:16][C:17]#[CH:18]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 224997916-But-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione

Product 1

HCID 16074361HCID 16074361, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of thiophenol (0.23 mL, 2.2 mmol), triethyl amine (0.156 mL, 1.1 mmol), and 6-but-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione (0.30 g, 1.1 mmol; prepared as described in step 1 above) in DMF (3 mL) was stirred at room temperature for 2 hours. The reaction was then concentrated by rotary evaporation, and then chromatographed (40 g silica gel, gradient elution from 40% EtOAc/Hexanes to 75% EtOAc/Hexanes) to yield the title compound (135 mg, 36%). 1H NMR (CDCl3): δ1.31-1.80 (m, 9H); δ1.96-2.00 (m, 2 H); δ2.03-2.11 (3H, m); δ2.85 (2H, dd, J1=17.94, J2=27.03); δ7.13-7.36 (5H, m). Anal. Calcd. for C20H22O3S.0.1 MeOH.0.15 CH2Cl2: C, 67.86; H, 6.38; S, 8.95. Found C, 68.08; H, 6.48; S, 8.52. ESIMS (M+Na+): 365.

Workup

  1. concentrationThe reaction was then concentrated by rotary evaporation
  2. customchromatographed
  3. wash(40 g silica gel, gradient elution from 40% EtOAc/Hexanes to 75% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-32556bbc638340dfb2996dccda1609b8
Source dataset
uspto-grants-2005_04
Patent number
US06878727B2

Reaction notes

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