Chlorotrimethylsilane → (4,5-Diacetoxy-6-acetoxymethyl-2-[5-isopropyl-2-(4-methoxy-benzyl)-thiophen-3-yloxy]-tetrahydro-pyran-3-yl) acetate

HRID 1445337

Reaction equation

HRID 1445337 reaction equation
[C:1]([O:4][CH:5]1[CH:10]([O:11][C:12](=[O:14])[CH3:13])[CH:9]([O:15][C:16](=[O:18])[CH3:17])[CH:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[O:24][C:25]1[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[S:27][C:26]=1[C:33](=O)[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)(=[O:3])[CH3:2].C[Si](C)(C)Cl.C([BH3-])#N.[Na+]>C(#N)C>[C:1]([O:4][CH:5]1[CH:10]([O:11][C:12](=[O:14])[CH3:13])[CH:9]([O:15][C:16](=[O:18])[CH3:17])[CH:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[O:24][C:25]1[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[S:27][C:26]=1[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 21045301(4,5-Diacetoxy-6-acetoxymethyl-2-[5-isopropyl-2-(4-methoxy-benzoyl)-thiophen-3-yloxy]-tetrahydro-pyran-3-yl) acetate

Product 1

HCID 21045302(4,5-Diacetoxy-6-acetoxymethyl-2-[5-isopropyl-2-(4-methoxy-benzyl)-thiophen-3-yloxy]-tetrahydro-pyran-3-yl) acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

630 mg of (4,5-diacetoxy-6-acetoxymethyl-2-[5-isopropyl-2-(4-methoxy-benzoyl)-thiophen-3-yloxy]-tetrahydro-pyran-3-yl) acetate were dissolved in 30 ml of acetonitrile and cooled to 0° C. in an ice bath. 1.31 ml of trimethylchlorosilane and 652 mg of sodium cyanoborohydride were added, the ice bath was removed and the reaction was stirred for 2 h. 100 ml of water were added to the reaction mixture, which was extracted twice with 70 ml of dichloromethane each time. The combined organic phases were washed with 50 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:1).

Workup

  1. customthe ice bath was removed
  2. addition100 ml of water were added to the reaction mixture, which
  3. extractionwas extracted twice with 70 ml of dichloromethane each time
  4. washThe combined organic phases were washed with 50 ml of saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:1)

Sources & evidence

ORD record
ord-f73d86f60a234e4c8299a158556fc0b4
Source dataset
uspto-grants-2010_02
Patent number
US07666848B2

Linked notes

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