Ammonium Chloride → HCID 12136225, compound

HRID 857957Notes

Reaction equation

HRID 857957 reaction equation
C1OCCOCCOCCOCCOCCOC1.[CH3:19][O:20][C:21]([CH2:23]P(=O)(OCC(F)(F)F)OCC(F)(F)F)=[O:22].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:48][C:49]([Si:52]([CH3:92])([CH3:91])[O:53][CH:54]([CH:59]([CH3:90])[CH:60]=[C:61]([CH3:89])[CH2:62][CH:63]([CH3:88])[CH:64]([O:80][Si:81]([C:84]([CH3:87])([CH3:86])[CH3:85])([CH3:83])[CH3:82])[CH:65]([CH3:79])[CH:66]([OH:78])[CH:67]([CH3:77])[CH2:68][O:69][CH2:70][C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)[CH:55]([CH3:58])[CH:56]=O)([CH3:51])[CH3:50].[NH4+].[Cl-]>C1(C)C=CC=CC=1>[CH3:19][O:20][C:21](=[O:22])/[CH:23]=[CH:56]\[C@H:55]([CH3:58])[C@H:54]([O:53][Si:52]([C:49]([CH3:51])([CH3:50])[CH3:48])([CH3:92])[CH3:91])[C@@H:59]([CH3:90])/[CH:60]=[C:61](/[CH3:89])\[CH2:62][C@H:63]([CH3:88])[C@@H:64]([O:80][Si:81]([C:84]([CH3:85])([CH3:86])[CH3:87])([CH3:83])[CH3:82])[C@H:65]([CH3:79])[C@@H:66]([OH:78])[C@@H:67]([CH3:77])[CH2:68][O:69][CH2:70][C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 184894Nsc 634137HCID 3251421Potassium bis(trimethylsilyl)amideHCID 86760328HCID 86760328, compound

Product 1

HCID 12136225HCID 12136225, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-20 °C

Procedure

18-Crown-6 (349 mg, 1.32 mmol, 2 eq) is added to a solution of bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate (355 mg, 1.78 mmol, 2.7 eq) in toluene (7 mL) at 23° C. and stirred for 5 min. The mixture is cooled to −20° C. KHMDS (1.78 mmol, 2.7 eq, 0.5 M in toluene) is added dropwise and stirred for 30 min. The mixture is warmed to 0° C. and stirred for 30 min. Then the mixture is cooled to −20° C., a solution of crude (2R,3R,4S,5Z,8S,9R, 10R, 11 S,12S)-3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-hydroxy-2,4,6,8,10,12-hexamethyl-13-(phenylmethoxy)-5-tridecenal in toluene (3 mL) is added to the mixture and stirred for 5 min. The mixture is warmed to 0° C. and stirred for 4 h. Saturated NH4Cl (15 mL) is added, and the resultant mixture is washed with brine, dried and concentrated. The crude product is chromatographed (10% EtOAc in hexane) to give 266 mg (two-step: 52%) of the desired compound as a colorless oil.

Workup

  1. stirringstirred for 30 min
  2. temperatureThe mixture is warmed to 0° C.
  3. stirringstirred for 30 min
  4. temperatureThen the mixture is cooled to −20° C.
  5. stirringstirred for 5 min
  6. temperatureThe mixture is warmed to 0° C.
  7. stirringstirred for 4 h
  8. washthe resultant mixture is washed with brine
  9. customdried
  10. concentrationconcentrated
  11. customThe crude product is chromatographed (10% EtOAc in hexane)

Sources & evidence

ORD record
ord-e4050c0c973140a7a25eed4d5bf2e029
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

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