Water → HCID 66740277, compound

HRID 1035690Notes

Reaction equation

HRID 1035690 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(=O)=O.[O:27]1[CH2:32]COCC1.C(N(C(C)C)CC)(C)C.[OH2:42]>CN(C)C1C=CN=CC=1.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:23]([O:22][C:20]([CH2:19][CH:16]1[CH2:17][CH2:18][CH:13]([C:10]2[CH:11]=[CH:12][C:7]([C:32]([OH:27])=[O:42])=[CH:8][CH:9]=2)[CH2:14][CH2:15]1)=[O:21])[CH3:24]

Participants

9

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 86662110HCID 86662110, compound

Product 1

HCID 66740277HCID 66740277, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
120 °C

Procedure

One third of the 3 g of ethyl [4-(4-trifluoromethanesulfonyloxyphenyl)cyclohexyl]acetate (3 g, 7.61 mmol, 1 eq.) is placed, respectively, in one third of the 18 mL of dioxane in three 20 mL microwave tubes. One third of each amount of the reagents molybdenum hexacarbonyl (1 g, 3.80 mmol, 0.5 eq.), 0.171 g of palladium acetate (II) (0.76 mmol, 0.1 eq.), 0.422 g of 1,1′-bis(diphenylphosphino)ferrocene (0.76 mmol, 0.1 eq.), 1.859 g of 4-dimethylaminopyridine (15.21 mmol, 2 eq.), 3.1 mL of diisopropylethylamine (17.49 mmol, 2.3 eq.) and 2.74 mL of water is successively and respectively added to each tube. The tubes are heated at 120° C. for 20 minutes in a Biotage microwave machine. The reaction media are filtered through Celite. The filtrate is diluted with 200 mL of dichloromethane and washed with twice 100 mL of saturated sodium carbonate solution. 10 mL of ethyl ether are added. After separation of the phases by settling, the aqueous phase is acidified to pH=1 with 5N hydrochloric acid solution and extracted with twice 200 mL of dichloromethane. The organic phase is concentrated to dryness to give 0.560 g of 4-(4-ethoxycarbonylmethylcyclohexyl)benzoic acid.

Workup

  1. additionrespectively added to each tube
  2. customThe reaction media
  3. filtrationare filtered through Celite
  4. additionThe filtrate is diluted with 200 mL of dichloromethane
  5. washwashed with twice 100 mL of saturated sodium carbonate solution
  6. addition10 mL of ethyl ether are added
  7. customAfter separation of the phases
  8. extractionextracted with twice 200 mL of dichloromethane
  9. concentrationThe organic phase is concentrated to dryness

Sources & evidence

ORD record
ord-d866ff04acd3429890da844feae297c4
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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