tert-Butanol → HCID 66588522, compound

HRID 1092440Notes

Reaction equation

HRID 1092440 reaction equation
C(O)(C)(C)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:28]([O:35][C@H:36]1[C@H:41]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C@@H:40]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C@H:39]([C:58]2[CH:63]=[CH:62][C:61]([Cl:64])=[C:60]([CH2:65][C:66]3[CH:71]=[CH:70][C:69]([CH2:72][CH3:73])=[CH:68][CH:67]=3)[CH:59]=2)[C@@H:38]([OH:74])[C@@H:37]1[CH2:75][O:76][CH2:77][C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C.[Cl-].[Na+].O>[CH2:28]([O:35][C@H:36]1[C@H:41]([O:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C@@H:40]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C@H:39]([C:58]2[CH:63]=[CH:62][C:61]([Cl:64])=[C:60]([CH2:65][C:66]3[CH:67]=[CH:68][C:69]([CH2:72][CH3:73])=[CH:70][CH:71]=3)[CH:59]=2)[C:38](=[O:74])[C@@H:37]1[CH2:75][O:76][CH2:77][C:78]1[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

9

Reactant 5

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 66588466HCID 66588466, compound

Product 1

HCID 66588522HCID 66588522, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of tert-butanol (28.2 μL, 296 μMol) in dichloromethane (4 mL) was added Dess-Martin Periodinane [1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one] (116 mg, 274 μMol), and the resulting mixture was stirred under argon at room temperature for 10 minutes. A solution of alcohol 4 (R=Et, mixture of isomers) in dichloromethane (2 mL) was added to the mixture and stirred at room temperature for 3 hours. The mixture was diluted with 4 mL ethyl acetate and stirred vigorously with aqueous 1.5:1:1 saturated sodium sulfite:saturated sodium bicarbonate:brine (3.5 mL) for a period of 1 hour. The phases were separated and the aqueous phase was re-extracted with ethyl acetate (3 mL). The combined organics were washed with brine (2 mL), dried (anhydrous Na2SO4), filtered, and evaporated. Preparative TLC using dichloromethane as the developing solvent afforded 91 mg (52%) of compound 14 as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.35-6.90 (m, 25H), 6.80 (m, 2H), 4.96 (m, 3H), 4.55 (m, 4H), 4.11 (m, 3H), 3.94 (m, 2H), 3.79 (m, 3H), 3.47 (s, 1H), 2.83 (m, 1H), 2.62 (q, J=7.8 Hz, 2H), 1.16 (t, J=7.5 Hz, 3H). LC-ESI-MS m/z 766 (M+H), 788 (M+Na).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. customThe phases were separated
  3. extractionthe aqueous phase was re-extracted with ethyl acetate (3 mL)
  4. washThe combined organics were washed with brine (2 mL)
  5. dry with materialdried (anhydrous Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-449b65cf448340c093fafa1d8c02fbb5
Source dataset
uspto-grants-2012_03
Patent number
US08129434B2

Reaction notes

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