Tetrahydrofuran → HCID 178443478, compound

HRID 1440519Notes

Reaction equation

HRID 1440519 reaction equation
Br[C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=O.C[C:15]([CH3:18])([O-])[CH3:16].[K+].C([SH:26])CCCCC.[CH2:27]1[CH2:31]OC[CH2:28]1>>[CH2:28]([C@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=[S:26])[CH2:27][CH2:31][CH2:16][CH2:15][CH3:18]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81061-HexanethiolHCID 23665647Potassium tert-butoxideHCID 54003829HCID 54003829, compound

Product 1

HCID 178443478HCID 178443478, compoundYield 36%

Conditions

Temperature
0 °C

Procedure

(S)-(-)-2-Bromodecanoic acid (125 mg, 0.50 mmol, [α]20D =-29,9° in MeOH) and potassium tert-butoxide (200 mg, 1.8 mmol) were mixed in 3 ml THF and cooled to 0° C. The reaction was not homogeneous. Hexanethiol (84 mg, 0.71 mmol) 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 52 mg (36% yield) of the desired product: [α]20D =+56.0° (c=0.015, MeOH); 1H NMR (CDCl3) δ3.22 (1H, dd, J=7.7, 7.3 Hz), 2.62 (2H, m), 1.85 (1H, m), 1.58 (2H, m), 1.25 (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-96ccd57048254a8a907a6c91f649d81b
Source dataset
uspto-grants-1996_03
Patent number
US05498786

Reaction notes

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