Ethyl Acetate → HCID 57835729, compound

HRID 1675288Notes

Reaction equation

HRID 1675288 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[O:7]1[CH2:11][CH2:10][C:9]([CH:12]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:13][C:14]([OH:16])=[O:15])=[N:8]1.Br[CH2:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[C:32]([CH3:37])([CH3:36])[CH2:31][CH2:30][C:29]2([CH3:39])[CH3:38].CCOC(C)=O>CS(C)=O.[Cl-].[Na+].O>[O:7]1[CH2:11][CH2:10][C:9]([CH:12]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:32]([CH3:37])([CH3:36])[CH2:31][CH2:30][C:29]([CH3:39])([CH3:38])[C:28]=4[CH:27]=3)=[CH:21][CH:22]=2)[CH2:13][C:14]([OH:16])=[O:15])=[N:8]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27355976-(Bromomethyl)-1,1,4,4-Tetramethyl-1,2,3,4-TetrahydronaphthaleneHCID 57835804HCID 57835804, compound

Product 1

HCID 57835729HCID 57835729, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
45 °C

Procedure

Cesium carbonate (108 mg, 0.33 mmol) was added into a mixture of 42.2 (25 mg, 0.11 mmol) and 6-(bromomethyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (76 mg, 0.27 mmol) in DMSO (1 mL). The mixture was stirred at 45° C. for 3 hours. After cooling, the mixture was treated with EtOAc (5 mL) and brine (5 mL). The organic layer was separated, washed with brine twice, dried and concentrated. The crude product was treated with THF (1 mL), MeOH (1 mL), water (0.5 mL) and NaOH (0.05 mL, 10N). The mixture was stirred at room temperature for 4 hours. The organic solvent was blown away by nitrogen, and the aqueous layer was acidified by HCl (0.18 mL, 3N). The aqueous layer was extracted with DCM. The organic layer was dried, concentrated and purified by flash chromatography to give 42 (15 mg). MS ESI (pos.) m/e: 436 (M+H). 1HNMR (CDCl3) δ 7.35 (m, 2H), 7.19 (m, 3H), 6.96 (d, 2H), 4.97 (s, 2H), 4.28 (m, 2H), 4.07 (t, 1H), 3.28 (dd, 1H), 2.79 (m, 3H), 1.71 (s, 4H), 1.30 (s, 12H).

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with brine twice
  4. customdried
  5. concentrationconcentrated
  6. additionThe crude product was treated with THF (1 mL), MeOH (1 mL), water (0.5 mL) and NaOH (0.05 mL, 10N)
  7. stirringThe mixture was stirred at room temperature for 4 hours
  8. extractionThe aqueous layer was extracted with DCM
  9. customThe organic layer was dried
  10. concentrationconcentrated
  11. custompurified by flash chromatography

Sources & evidence

ORD record
ord-90dc10494bc249919df082c556cc4de6
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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