Tetrahydrofuran → HCID 86702585, compound

HRID 1746818Notes

Reaction equation

HRID 1746818 reaction equation
O1CCCC1.C[Si](C)(C(C)(C)C)[O:8][CH2:9][C@@H:10]1[C@@H:18]2[C@@H:13]([S:14][C@@H:15]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:16][CH2:17]2)[CH2:12][C@H:11]1[O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>C(OCC)(=O)C>[OH:8][CH2:9][C@@H:10]1[C@@H:18]2[C@@H:13]([S:14][C@@H:15]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:16][CH2:17]2)[CH2:12][C@H:11]1[O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11078149TBAF tetrahydrofuranHCID 86702586HCID 86702586, compound

Product 1

HCID 86702585HCID 86702585, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran (74 mL) solution of the compound 9 (7.3 g) was added a 1 M tetrabutylammonium fluoride/tetrahydrofuran solution (27 mL), and the mixture was stirred for 3 hours. The reaction liquid was diluted with ethyl acetate (380 mL), washed with water (740 mL) and a saturated saline (380 mL). Further the aqueous layer was extracted with ethyl acetate (100 mL). The organic layers were combined, dried with anhydrous sodium sulfate, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1). The resulting compound was purified again by silica gel column chromatography (dichloromethane:ethyl acetate=4:1→ethyl acetate) to obtain a titled compound (3.24 g) having the following physical property values.

Workup

  1. customThe reaction liquid
  2. washwashed with water (740 mL)
  3. extractionFurther the aqueous layer was extracted with ethyl acetate (100 mL)
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)
  7. customThe resulting compound was purified again by silica gel column chromatography (dichloromethane:ethyl acetate=4:1→ethyl acetate)

Sources & evidence

ORD record
ord-b7491afb40ec4033a64b1d1e814d7204
Source dataset
uspto-grants-2015_10
Patent number
US09150537B2

Reaction notes

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