Chlorotrimethylsilane → HCID 11461188, compound

HRID 1992574Notes

Reaction equation

HRID 1992574 reaction equation
[OH:1][C:2]1[C:6]([CH3:15])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[S:5][C:4](=[O:16])[CH:3]=1.C(N(CC)CC)C.[CH3:24][Si:25](Cl)([CH3:27])[CH3:26]>>[CH3:15][C:6]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[S:5][C:4](=[O:16])[CH:3]=[C:2]1[O:1][Si:25]([CH3:27])([CH3:26])[CH3:24]

Participants

4

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 1355380184-hydroxy-5-Methyl-5-octylthiophen-2(5H)-one

Product 1

HCID 11461188HCID 11461188, compound

Procedure

To 32 (46 mg, 0.19 mmol) dissolved in hexanes was added triethylamine (43 μL, 0.31 mmol) and trimethylsilylchloride (36 μL, 0.29 mmol) and the solution was allowed to stir at room temperature for 4 h. The mixture was filtered over celite and evaporated to provide 5-methyl-5-octyl-4-trimethylsilanyloxy-5-H-thiopen-2-one which was redissolved in CH2Cl2 (0.4 mL). To this mixture was added isopropyl isocyanate (19.2 mL, 0.19 mmol) and the solution was allowed to stir at room temperature for 2 hours. NH4Cl(sat) (5 mL) was added and the mixture was extracted with CH2Cl2 (3×10 mL). The organics were combined, dried (MgSO4), filtered and evaporated to give crude 71. Flash chromatography (20% EtOAc/2% AcOH/Hexanes) gave pure 71 (35 mg, 60%). 1H NMR (300 MHz, CDCl3) δ 0.85 (t, J=7.0 Hz, 3H), 1.14-1.24 (m, 17H), 1.45 (m, 1H), 1.63 (s, 3H), 1.76-1.79 (m, 2H), 3.81-3.88 (m, 1H), 5.16 (d, J=7 Hz, 1H), 6.33 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 13.9, 20.4, 22.5, 22.8, 25.1, 25.9, 29.1, 29.3, 29.5, 31.8, 38.7, 44.0, 60.2, 111.6, 149.7, 176.2, 194.5.

Workup

  1. filtrationThe mixture was filtered over celite
  2. customevaporated

Sources & evidence

ORD record
ord-4d23b1184a6540329323f467bac8369f
Source dataset
uspto-grants-2010_01
Patent number
US07649012B2

Reaction notes

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