Water → 2-Naphthalenemethanol, 1,4-dimethoxy-3-methyl-

HRID 968474Notes

Reaction equation

HRID 968474 reaction equation
[CH2:1]([Li])CCC.[CH3:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH3:19])=[CH:10][C:9]=1[CH2:20][OH:21].CI.O>C1COCC1>[CH3:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH3:19])=[C:10]([CH3:1])[C:9]=1[CH2:20][OH:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10704023(1,4-Dimethoxynaphthalen-3-yl)methanolHCID 178418339Butyllithium

Product 1

HCID 105615442-Naphthalenemethanol, 1,4-dimethoxy-3-methyl-Yield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (7.3 mL, 18.3 mmol, 2.5 M in hexanes) was added dropwise via syringe to a solution of 23a (1.00 g, 4.58 mmol) in THF (30 mL) at −78° C. under argon. The solution was slowly warmed to room temperature and stirred for 1 h. Methyl iodide (0.34 mL, 5.50 mmol) was added dropwise and the solution was stirred for 20 min. Water (8 mL) was added and the mixture was extracted with EtOAc (4×). The combined organic layers were dried (MgSO4), filtered and evaporated. Column chromatography of the crude product (45:55 EtOAc:hexanes) afforded 23b (0.61 g, 57%) as a yellow solid; Rf=0.59 (45:55 EtOAc:hexanes); mp=116–117° C.; lit mp=118–121,C25; 1H NMR (CDCl3): δ 8.07 (dd, 2H), 7.51 (m, 2H), 4.94 (s, 2H), 3.98 (s, 3H), 3.88 (s, 3H), 2.52 (s, 3H), 1.73 (bs, 1H).

Workup

  1. stirringthe solution was stirred for 20 min
  2. extractionthe mixture was extracted with EtOAc (4×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-730ff0a26ce8410bb38f711fb5f7c7f8
Source dataset
uspto-grants-2007_12
Patent number
US07304046B2

Reaction notes

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