Sodium hydride → HCID 19874747, compound

HRID 465629Notes

Reaction equation

HRID 465629 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][CH2:13][OH:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:16][C:17]([O:19][C:20]([CH3:23])(C)C)=[O:18]>O1CCOCC1>[CH2:3]([O:10][CH2:11][CH2:23][CH2:20][O:19][C:17](=[O:18])[CH2:16][O:14][CH2:13][CH2:12][CH2:11][O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 3479713-Benzyloxy-1-propanol

Product 1

HCID 19874747HCID 19874747, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of sodium hydride (0.24 g, 6 mmol) in dioxane (20 ml) is added 3-benzyloxypropan-1-ol (1.0, 6 mmol) and the mixture is allowed to stir at room temperature for 1 hour. t-Butyl bromoacetate (1.05 g, 6.5 mmol) is added slowly and the mixture is allowed to stir for 18 hours. The solvent is evaporated and saturated ammonium chloride (20 ml) is added. The mixture is extracted with methylene chloride (3×20 ml) and the combined organic extracts are dried, filtered and evaporated. Purification by flash column chromatography on silica gel using ethyl acetate/hexane (1:4) as eluent yields 3-benzyloxypropyl-2-[(3-benzyloxypropyl)oxy]-acetate; 1H NMR (CDCl3): δ7.3 (m, 10H), 4.48 (q,4H), 4.27 (t,8 Hz,2H), 4.0 (s,2H), 3.56 (m,6H), 1.92 (m,2H).

Workup

  1. stirringto stir for 18 hours
  2. customThe solvent is evaporated
  3. additionsaturated ammonium chloride (20 ml) is added
  4. extractionThe mixture is extracted with methylene chloride (3×20 ml)
  5. customthe combined organic extracts are dried
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ab24e6d4672148ffbf30d5c0c79d07c2
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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