Acetic Acid → HCID 68862803, compound

HRID 898886Notes

Reaction equation

HRID 898886 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=O)[CH2:7][CH2:6]2.[CH2:14]([NH2:16])[CH3:15].C1COCC1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[F:42][C:43]([F:59])([F:58])[O:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][C:52](=O)[O:53]C(Cl)C)=[CH:47][CH:46]=1>C(Cl)Cl.C1(C)C=CC=CC=1.CCOCC>[F:42][C:43]([F:58])([F:59])[O:44][C:45]1[CH:46]=[CH:47][C:48]([O:51][C:52](=[O:53])[N:16]([CH2:14][CH3:15])[CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)=[CH:49][CH:50]=1

Participants

11

Reactant 7

HCID 176Acetic AcidHCID 6341EthylamineHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-oneHCID 5049666Sodium triacetoxyborohydrideHCID 68859918HCID 68859918, compound

Product 1

HCID 68862803HCID 68862803, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-methoxy-2-tetralone (950 mg; 5.39 mmol), 2 M of ethylamine in THF (5.4 mL; 10.78 mmol) and acetic acid (648 mg; 10.78 mmol) in CH2Cl2 (5 mL) was added sodium triacetoxyborohydride (2.29 g; 10.78 mmol). The reaction mixture was stirred at RT for 3 h, then 1N solution of NaOH was added, and extracted with ether (3 times). The combined organic extracts were dried over Na2SO4, and the solvent was removed under reduced pressure to give a light-yellow oil. This oil was added to a solution of carbonic acid 1-chloro-ethyl ester 4-trifluoromethoxy-phenyl ester (1.23g; 4.31 mmol) in toluene(8 mL), and the reaction mixture was stirred for 1 h at RT followed by 1 h at 90° C. The reaction was allowed to cool to RT, diluted with Et2O and washed with 1 N of aqueous HCl and saturated NaHCO3. The organic extract was dried over Na2SO4, and the solvent was removed under reduced pressure. Flash chromatography of the residue with a gradient of hexane-CH2Cl2 gave 1.05 g (48%) of ethyl-(6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid 4-trifluoromethoxy-phenyl ester as a white solid.

Workup

  1. extractionextracted with ether (3 times)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. customthe solvent was removed under reduced pressure
  4. customto give a light-yellow oil
  5. stirringthe reaction mixture was stirred for 1 h at RT
  6. waitfollowed by 1 h at 90° C
  7. temperatureto cool to RT
  8. washwashed with 1 N of aqueous HCl and saturated NaHCO3
  9. extractionThe organic extract
  10. dry with materialwas dried over Na2SO4
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9e107006383043709bd6d9359606a419
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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