HCID 23440844, compound → HCID 23440710, compound

HRID 2304663Notes

Reaction equation

HRID 2304663 reaction equation
[C:1]1([NH:11][C:12](=O)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:15]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>O1CCCC1>[C:1]1([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:15]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 23440844HCID 23440844, compound

Product 1

HCID 23440710HCID 23440710, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-naphthyl-2-[3-(phenylmethoxy)phenyl]acetamide (3.00 g, 8.16 mmol) in tetrahydrofuran (25 mL) under nitrogen was added a solution of 1.0 M borane-tetrahydrofuran complex in tetrahydrofuran (12.3 mL, 12.3 mmol) and heated to reflux for 5 hours. The reaction was quenched with a 5% hydrochloride solution. After stirring 30 minutes, the reaction was basified with a 10% sodium carbonate solution and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated to provide the title compound (2.724 g, 94% yield): 1H NMR (CDCl3) 7.78 (d, 1H), 7.67 (d, 1H), 7.18-7.46 (m, 10H), 6.89 (m, 3H), 6.66 (d, 1H), 5.01 (s, 2H), 4.40 (br, 1H), 3.55 (t, 2H), 3.05 (t, 2H); ES-MS (m/z) 354 [M]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. customThe reaction was quenched with a 5% hydrochloride solution
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-47f46632f1eb4d3eb3b57d34ee95e692
Source dataset
uspto-grants-2002_08
Patent number
US06436923B1

Reaction notes

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