Lithium Hexamethyldisilazide → HCID 60099787, compound

HRID 1348917Notes

Reaction equation

HRID 1348917 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])[C:14]([O-])=[O:15].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH:7]([C:14](=[O:15])[C:13]([O:18][CH2:19][CH3:20])=[O:17])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneHCID 21943339Ethanedioic acid, monoethyl ester

Product 1

HCID 60099787HCID 60099787, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-hydroxy-1-tetralone (10.4 g, 0.064 mol) and ethyl oxalate (17.4 mL, 0.128 mol) in THF (100 mL) was added dropwise lithium bis(trimethylsilyl)amide (1M in THF, 130 mL). The slurry was stirred overnight and a solid was filtered. The solid was dissolved in water and made acidic to pH 2.5 with 3 N HCl, precipitating a waxy solid. The waxy solid was extracted into EtOAc, dried (MgSO4), and concentrated in vacuo leaving a dark solid (15.7 g). The solid was purified by chromatography on silica gel, eluting with 15% EtOAc/hexanes to give a yellow solid (5.9 g). The solid was recrystallized from EtOAc/hexanes to give the product as a yellow solid, 3.7 g (22% yield). FABHRMS m/z 263.0925 (M+H, C14H15O5 requires 263.0919). 1H NMR (CDCl3/300 MHz) 7.93 (d, 1H); 6.80 (d of d, 1H); 6.68 (s, 1H); 5.72 (s, 1H); 4.39 (q, 2H); 3.00-2.75 (m, 4H); 1.40 (t, 3H).

Workup

  1. filtrationa solid was filtered
  2. dissolutionThe solid was dissolved in water
  3. customprecipitating a waxy solid
  4. extractionThe waxy solid was extracted into EtOAc
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c3169ac99e146cf99bcd5e0fb1b396f
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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