tert-Butanol → HCID 65143109, compound

HRID 2207737Notes

Reaction equation

HRID 2207737 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](C(O)=O)=[CH:9][C:4]=2[CH2:3][CH2:2]1.C([N:15](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:37](=[O:40])([O-])[OH:38].[Na+].[C:42](O)([CH3:45])([CH3:44])[CH3:43]>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:15][C:37](=[O:40])[O:38][C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 6765832,3-Dihydrobenzo(b)furan-5-carboxylic acid

Product 1

HCID 65143109HCID 65143109, compound

Conditions

Temperature
90 °C

Procedure

To a mixture of 2,3-dihydro-1-benzofuran-5-carboxylic acid (5.08 g), triethylamine (5.18 mL) and tert-butanol (91.9 mL) was added diphenylphosphoryl azide (8.00 mL), followed by stirring at 90° C. for 5 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1 to 5:1) to obtain tert-butyl (2,3-dihydro-1-benzofuran-5-yl)carbamate (4.74 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe insoluble materials were separated by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1 to 5:1)

Sources & evidence

ORD record
ord-db23de0e917a4ce69364aa9224f71e36
Source dataset
uspto-grants-2016_06
Patent number
US09376449B2

Reaction notes

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