Tetrahydrofuran → HCID 178443478, compound

HRID 1440518Notes

Reaction equation

HRID 1440518 reaction equation
Br[C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]CC)[C:3](O)=O.C(=O)([O-])[O-:15].[Cs+].[Cs+].[CH2:20]([SH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[CH2:27]1COC[CH2:28]1>>[CH2:22]([C@H:21]([CH2:3][CH2:2][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:20]([OH:15])=[S:26])[CH2:23][CH2:24][CH2:25][CH2:27][CH3:28]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81061-HexanethiolHCID 10796Cesium carbonateHCID 54003829HCID 54003829, compound

Product 1

HCID 178443478HCID 178443478, compoundYield 80%

Conditions

Temperature
0 °C

Procedure

(S)-(-)-2-Bromodecanoic acid (250 mg, 1 mmol) and cesium carbonate (980 mg, 3 mmol) were mixed in 5 ml THF and cooled to 0° C. The reaction was not homogeneous. Hexanethiol was added dropwise. The reaction was allowed to warm to rt and stirred under N2 for 18 hours. The reaction was quenched with 100 ml 1N HCl and extracted with ethyl acetate (3×50 ml). The concentrated organic phase was purified by silica gel column chromatography (eluent: 100% CH2Cl2) to yield 230 mg (80% yield) of the desired product: [α]20D =+57.9 (c=0.022, MeOH); 1H NMR (CDCl3) δ3.21 (1H, dd, J =6.9, 7.0 Hz), 2.62 (2H, m), 1.84 (1H, m), 1.58 (2H, m), 1.26 (19H, m), 0.87 (6H, m).

Workup

  1. temperatureto warm to rt
  2. customThe reaction was quenched with 100 ml 1N HCl
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. customThe concentrated organic phase was purified by silica gel column chromatography (eluent: 100% CH2Cl2)

Sources & evidence

ORD record
ord-7b56f2d6f98547358999f1df61d66651
Source dataset
uspto-grants-1996_03
Patent number
US05498786

Reaction notes

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