Sodium hydride → HCID 58288703, compound

HRID 471358Notes

Reaction equation

HRID 471358 reaction equation
[C:1]1([OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:16]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[O:17]>CN(C=O)C>[C:16](=[O:17])([O:12][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][C:16](=[O:17])[O:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH:4]=[CH:3][CH:2]=1)[O:18][CH2:19][CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62365Isobutyl chloroformateHCID 684381,8-Dihydroxynaphthalene

Product 1

HCID 58288703HCID 58288703, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a round-bottom flask is charged naphthalene-1,8-diol (4.0 g, 25 mmol), and anhydrous DMF (50 ml). The flask is immersed in an ice-water bath, and 60% sodium hydride in mineral oil (2.4 g, 60 mmol) is added in portions. The mixture is stirred for an hour. Isobutyl chloroformate (8.2 g, 60 mmol) is added dropwise. After gradually warming to room temperature, the mixture is stirred overnight. The mixture is poured into ice-cold water and extracted with ether three times. The combined ether extracts are washed with water, then brine, and then dried over magnesium sulfate. After filtration, the filtrate is concentrated, and the residue is purified by flash column chromatography on silica gel to yield 2.8 g (31%) of the product as a light-grey solid. 1H NMR (400 MHz, CDCl3, ppm) δ 7.79 (dd, 2H, J=1.2, 8.0 Hz), 7.47 (dd, 2H, J=7.6, 8.0 Hz), 7.26 (dd, 2H, J=1.2, 7.6 Hz), 4.07 (d, 4H, J=6.8 Hz), 2.07 (m, 2H), 1.00 (d, 12 H, J=6.8 Hz).

Workup

  1. customThe flask is immersed in an ice-water bath
  2. stirringthe mixture is stirred overnight
  3. additionThe mixture is poured into ice-cold water
  4. extractionextracted with ether three times
  5. washThe combined ether extracts are washed with water
  6. dry with materialbrine, and then dried over magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate is concentrated
  9. customthe residue is purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-d3cdfae8388d4115a2bf2124868a9645
Source dataset
uspto-grants-2014_01
Patent number
US08633126B2

Reaction notes

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