Dimethylformamide → HCID 86039940, compound

HRID 2099595Notes

Reaction equation

HRID 2099595 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2I)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])(C)(C)C.CCCCC.CN(C)CCN(C)C.CN(C)[CH:40]=[O:41]>CCOCC.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[CH:40]=[O:41])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8003PentaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 18536110HCID 18536110, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 86039940HCID 86039940, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 7-benzyloxy-1-iodo-naphthalene (4.60 g, 12.77 mmol) in ether (120 mL) is added 1.7 M tert-butyl-lithium in pentane (8.26 mL, 14.0 mmol) at −78° C. under nitrogen atmosphere and the resulting mixture is stirred for one hour while being warmed up to 5° C. The mixture is cooled to −78° C. again before tetramethylethylene-diamine (1.93 mL, 1.49 g, 12.79 mmol) is added. The mixture is stirred for 10 minutes before N, N-dimethylformamide (0.99 mL, 0.93 g, 12.78 mmol) is added. The mixture is gradually warmed up to room temperature and stirred over night. Ethyl acetate is added to reaction mixture, washed with saturated ammonium chloride, dried over sodium sulfate, filtered and concentrated. The crude product is purified by silica gel chromatography (Hexanes/EtOAc=20/1) to give 7-benzyloxy-naphthalene-1-carbaldehyde (1.95 g, 58.3% yield); 1H NMR 400 Hz (CDCl3) δ 5.27 (s, 2H), 7.33 (m, 2H), 7.42 (m, 2H), 7.52 (m, 3H), 7.83 (d, J=8.98 Hz, 1H), 7.95 (d, J=7.11 Hz, 1H), 8.03 (d, J=8.10 Hz, 1H), 10.32 (s, 1H); MS m/z (M+H+) 263.05.

Workup

  1. additionis added
  2. additionis added
  3. temperatureThe mixture is gradually warmed up to room temperature
  4. stirringstirred over night
  5. washwashed with saturated ammonium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by silica gel chromatography (Hexanes/EtOAc=20/1)

Sources & evidence

ORD record
ord-edb74765b95a4301a130021bf06ab12c
Source dataset
uspto-grants-2009_08
Patent number
US07569593B2

Reaction notes

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