Water → HCID 22452670, compound

HRID 2185890Notes

Reaction equation

HRID 2185890 reaction equation
I[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4](C(OC)=O)[C:3]=1[O:16][CH3:17].[H-].[Na+].COS([O:25][CH3:26])(=O)=O.O.CN([CH:31]=[O:32])C>CCOCC>[CH3:17][O:16][C:3]1[CH:4]=[C:5]([C:31]([O:25][CH3:26])=[O:32])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:2]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 22452654HCID 22452654, compound

Product 1

HCID 22452670HCID 22452670, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl 3-hydroxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (Example 6 subpart (c)) (1.38 g, 6.69 mmol) in DMF (30 mL) was added NaH (0.32 g, 8.0 mmol). After stirring at room temperature for 1 h, dimethylsulfate (0.76 mL, 8.0 mmol) was added, the mixture stirred at room temperature for 1 h and water and Et2O was added. The separated organic layer was washed with brine, water, dried (MgSO4), filtered and concentrated. Following flash chromatography methyl 3-methoxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate was obtained as a colorless oil (900 mg, 61%). 1H NMR (CDCl3) δ 7.21 (d, 1H), 6.78 (d, 1H), 3.87 (s, 3H), 3.80 (s, 3H), 2.97 (s, 2H), 2.79 (s, 2H), 1.76 (m, 4H); MS m/z 221.1 (M+H).

Workup

  1. stirringthe mixture stirred at room temperature for 1 h
  2. washThe separated organic layer was washed with brine, water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7c409a46a51b4534bb8e22fa59918120
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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