2-(2-Bromoethoxy)tetrahydro-2H-pyran → HCID 59279574, compound

HRID 1921210Notes

Reaction equation

HRID 1921210 reaction equation
C[C:2]([CH3:5])([O-:4])C.[K+].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C:8]1=[O:16].Br[CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1>C1COCC1>[O:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH:21]1[O:20][CH2:19][CH2:18][C:9]1([CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:5][CH2:2][O:4]2)[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:7][C:8]1=[O:16]

Participants

5

Reactant 3

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 321710OxindoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 59279574HCID 59279574, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (10.1 g, 90.1 mmol) was added to a solution of oxindole (3.00 g, 22.5 mmol) in THF (50 mL) at −75° C. and the mixture was allowed to warm to ambient temperature. After 1 h, the reaction was cooled to −75° C. and 2-(2-bromoethoxy)tetrahydro-2H-pyran (7.15 mL, 47.3 mmol) was added dropwise over 10 min. After 18 h, the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL). The layers were separated and the aqueous layer was further extracted with EtOAc (2×50 mL). The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 80:20, gave the title compound. MS: m/z=390 (M+1).

Workup

  1. temperaturethe reaction was cooled to −75° C.
  2. waitAfter 18 h
  3. customthe mixture was partitioned between EtOAc (100 mL) and H2O (100 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was further extracted with EtOAc (2×50 mL)
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel chromatography
  10. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-2f082a09a39f42509e82568d5742a87c
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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