Acetonitrile → (S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-formylnaphthalen-2-yl)acetate

HRID 514023Notes

Reaction equation

HRID 514023 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH2:20]N(C)C)=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:35]CC1.[C:39](#N)[CH3:40]>>[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH:20]=[O:35])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:7]([O:9][CH2:39][CH3:40])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 82029Methyl morpholine oxide2×HCID 56601917(S)-2-tert-Butoxy-2-(1-(4-chlorophenyl)-3-(dimethylaminomethyl) naphthalen-2-yl)acetic acid

Product 1

HCID 86691536(S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-formylnaphthalen-2-yl)acetateYield 64%

Procedure

To a solution of (S)-ethyl 2-(3-(bromomethyl)-1-(4-chlorophenyl)naphthalen-2-yl)-2-tert-butoxyacetate from Example 22 (200 mg, 0.408 mmol) in acetonitrile (4 mL) was added N-methylmorpholine N-oxide (478 mg, 4.08 mmol) and 4 Å molecular sieves (200 mg). The reaction mixture was stirred at room temperature for 2 h. Additional N-methylmorpholine N-oxide (500 mg, 4.27 mmol) was added and the reaction mixture was stirred at room temperature for another 2 h. The reaction mixture was then filtered and the organics washed with sat. NaHCO3, extracted by DCM, dried over MgSO4. The organic layer was then filtered, concentrated down and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to provide 110 mg (64%) of the desired product. 1H-MNR 400 MHz (CDCl3) δ: 10.82 (s, 1H), 8.55 (s, 1H), 8.01 (d, J=4 Hz, 1H), 7.55-7.23 (m, 7H), 5.19 (s, 1H), 4.17-4.13 (m, 2H), 1.22 (t, J=7 Hz, 3H), 1.04 (s, 9H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for another 2 h
  2. filtrationThe reaction mixture was then filtered
  3. washthe organics washed with sat. NaHCO3
  4. extractionextracted by DCM
  5. dry with materialdried over MgSO4
  6. filtrationThe organic layer was then filtered
  7. concentrationconcentrated down
  8. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3e1737be104e4eceb0f26ac6c104ed99
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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