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Hexane → Tert-butyl {4-[2-(benzyloxy)-2-oxoethyl]phenoxy}acetate

HRID 266746
Notes
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Reaction equation

HRID 266746 reaction equation
[H-].[Na+].CCCCCC.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:12][CH:11]=1.Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CN(C=O)C>[CH2:20]([O:19][C:17]([CH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:15][CH:14]=1)=[O:18])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 11107524Benzyl 2-(4-hydroxyphenyl)acetate

Product 1

HCID 68357704Tert-butyl {4-[2-(benzyloxy)-2-oxoethyl]phenoxy}acetate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
4 °C

Procedure

Sodium hydride (50% w/w dispersion in mineral oil, 2.1 g) was treated under argon with repeated washes of hexane. The oil-free residue was suspended in dry DMF (130 ml) and the product from step (i) (10 g) added in three portions to the cooled (4° C.) stirred mixture. Stirring was continued for a further 15 minutes when tertiary butyl bromoacetate (7.0 ml) was added dropwise over 15 minutes. After 1 hour at 4° C., the mixture was stirred for 6 hours at ambient temperature. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate and water. The aqueous phase was re-extracted with further ethyl acetate and the combined organic phases washed with water and brine, then dried (MgSO4) and evaporated. The residue, after purification by flash chromatography on silica eluting with dichloromethane, gave tertiary butyl 4-(benzyloxycarbonylmethyl)phenoxyacetate, 7.5 g, as a colourless oil: NMR (CDCl3) d 7.31(5H, m), 7.20(2H, m), 6.85(2H, m), 5.12(2H, s), 4.49(2H, s), 3.60(2H, s), 1.48(9H, s); m/e 356 (M*)+.

Workup

  1. stirringStirring
  2. waitAfter 1 hour at 4° C.
  3. stirringthe mixture was stirred for 6 hours at ambient temperature
  4. customThe solvent was evaporated in vacuo
  5. customthe residue partitioned between ethyl acetate and water
  6. extractionThe aqueous phase was re-extracted with further ethyl acetate
  7. washthe combined organic phases washed with water and brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue, after purification by flash chromatography on silica eluting with dichloromethane

Sources & evidence

ORD record
ord-cf463ee37b794817af2fb5576ccd7b1a
Source dataset
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05652242

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes