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Potassium Carbonate → [(2,3-Dihydro-3-oxo-1H-naphtho[2,1-b]pyran-8-yl)oxy]acetic Acid 1,1-Dimethylethyl Ester

HRID 1648104
Notes
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Reaction equation

HRID 1648104 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH2:11][CH2:10][C:9](=[O:16])[O:8][C:7]=1[CH:6]=[CH:5]2.Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:23][C:22]([O:21][C:19](=[O:20])[CH2:18][O:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH2:11][CH2:10][C:9](=[O:16])[O:8][C:7]=1[CH:6]=[CH:5]2)([CH3:25])[CH3:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate2×HCID 199219571,2-Dihydro-8-hydroxy-3H-naphtho[2,1-b]pyran-3-one

Product 1

HCID 54520651[(2,3-Dihydro-3-oxo-1H-naphtho[2,1-b]pyran-8-yl)oxy]acetic Acid 1,1-Dimethylethyl EsterYield 91%

Reagents, catalysts & solvents 1

HCID 6569
Methyl Ethyl Ketone
Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.18 g (10.2 mmol) of 1,2-dihydro-8-hydroxy-3H-naphtho[2,1-b]pyran-3-one from the preceding example, 4.84 g (24.8 mmol) of t-butyl bromoacetate, 5.63 g (40.7 mmol) of anhydrous granular potassium carbonate and 55.5 mL of 2-butanone was heated at 60° C. for 24 hr. A second portion of t-butyl bromoacetate (0.5 mL, 3.1 mmol) was added and the reaction was allowed to proceed for another 17 hr. After being cooled to room temperature, the mixture was filtered and the solids were washed with ethyl acetate and ether. The filtrate and washes were combined and concentrated in vacuo, and the crude product was flash chromatographed on 360 g of silica gel, eluting with hexane-ethyl acetate (7:1 then 6:1) affording 3.04 g (91.0%) of the title compound as a white solid, mp 95°-96° C.

Workup

  1. temperatureAfter being cooled to room temperature
  2. filtrationthe mixture was filtered
  3. washthe solids were washed with ethyl acetate and ether
  4. concentrationconcentrated in vacuo
  5. customchromatographed on 360 g of silica gel
  6. washeluting with hexane-ethyl acetate (7:1

Sources & evidence

ORD record
ord-d966d50141bb4db688e42da38fa61368
Source dataset
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05434186

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes