tert-Butanol → HCID 66740215, compound

HRID 1035732Notes

Reaction equation

HRID 1035732 reaction equation
FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=2)[CH2:9][CH:8]=1)(=O)=O.CCN(C(C)C)C(C)C.[C:35]([OH:39])([CH3:38])([CH3:37])[CH3:36].[O:40]1CCOC[CH2:41]1>CN(C1C=CN=CC=1)C.ClCCl.C(=[Mo](=C=O)(=C=O)(=C=O)(=C=O)=C=O)=O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:35]([O:39][C:41]([C:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=2)[CH2:9][CH:8]=1)=[O:40])([CH3:38])([CH3:37])[CH3:36]

Participants

10

Reactant 4

HCID 6386tert-ButanolHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 86662119HCID 86662119, compound

Product 1

HCID 66740215HCID 66740215, compound

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178521658HCID 178521658, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

1 g of ethyl 4-(4-trifluoromethanesulfonyloxycyclohex-3-enyl)benzoate is placed in 10 mL of dioxane, which is placed in two microwave tubes. 349 mg of hexacarbonylmolybdenum (1.32 mmol, 0.5 eq.), 59 mg of palladium diacetate (0.26 mmol, 0.1 eq.), 147 mg of DPPF (0.26 mmol, 0.1 eq.), 646 mg of DMAP (5.29 mmol, 2 eq.), 1.06 mL of DIEA (6.08 mmol, 2.3 eq.) and 2.53 mL of tert-butanol (26.43 mmol, 10 eq.), which are placed in two tubes, are successively added. The tubes are sealed and heated by microwave at 120° C. for 10 minutes. The reaction medium is diluted with dichloromethane and washed with aqueous 1N HCl solution. The organic phases are dried over sodium sulfate, filtered and evaporated. The residue is chromatographed on silica gel, eluting with a gradient of ethyl acetate in heptane ranging from 15% to 20%. 0.66 g of ethyl 4-(4-tert-butoxycarbonylcyclohex-3-enyl)-benzoate is obtained.

Workup

  1. additionare successively added
  2. customThe tubes are sealed
  3. washwashed with aqueous 1N HCl solution
  4. dry with materialThe organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed on silica gel
  8. washeluting with a gradient of ethyl acetate in heptane ranging from 15% to 20%

Sources & evidence

ORD record
ord-7e28915d9a7a4b4ba5d0f512b1db7beb
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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