Pyridine, hydrofluoride (1:1) → HCID 11955174, compound

HRID 9236Notes

Reaction equation

HRID 9236 reaction equation
C1C=CN=CC=1.F.[CH3:8][O:9][C:10](=[O:52])[CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][C@H:17]1[C@H:21]([Cl:22])[CH2:20][C@@H:19]([O:23][Si](C(C)(C)C)(C)C)[C@@H:18]1[C:31]1[CH:36]=[CH:35][C:34]([CH:37]([O:44][Si](C(C)(C)C)(C)C)[CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:33][CH:32]=1>CC#N>[CH3:8][O:9][C:10](=[O:52])[CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][C@H:17]1[C@H:21]([Cl:22])[CH2:20][C@@H:19]([OH:23])[C@@H:18]1[C:31]1[CH:32]=[CH:33][C:34]([CH:37]([CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[OH:44])=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 69595693HCID 69595693, compound

Product 1

HCID 11955174HCID 11955174, compoundYield 232.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

HF-pyridine (0.60 mL) was added to a 0° C. CH3CN solution of chloride 6-2 (24 mg, 20%) and the mono TBS derivative (36 mg, 36%). The reaction was stirred for 1 h, and then was quenched by addition of saturated NaHCO3 solution. The mixture was extracted with dichloromethane (3×30 mL) and the combined dichloromethane solution dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (20% ethyl acetate/hexanes) gave the title diol 6-3 (37 mg, 93%).

Workup

  1. customwas quenched by addition of saturated NaHCO3 solution
  2. extractionThe mixture was extracted with dichloromethane (3×30 mL)
  3. dry with materialthe combined dichloromethane solution dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography on silica gel (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9f9946512fca429383854066dd37fe03
Source dataset
uspto-grants-2006_08
Patent number
US07091231B2

Reaction notes

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