Pentane → HCID 58914714, compound

HRID 1297765Notes

Reaction equation

HRID 1297765 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:17])[C:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:6]([CH3:8])[CH:7]=1.C([Li])(C)(C)C.CCCCC.[CH2:28]([N:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37](=[O:44])[C:36]1=[O:45])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>COCCOC>[CH2:28]([N:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]([C:2]2[CH:3]=[C:4]([CH3:17])[C:5]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:6]([CH3:8])[CH:7]=2)([OH:44])[C:36]1=[O:45])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 2647341-BenzylisatinHCID 229631332-(Benzyloxy)-5-bromo-1,3-dimethylbenzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 58914714HCID 58914714, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

Dissolve 5-bromo-1,3-dimethyl-2-(phenylmethoxy)-benzene (2.56 g, 8.8 mmol) in ethylene glycol dimethyl ether (40 mL) under nitrogen. Cool to −70° C. with a dry ice/acetone bath and add slowly a 1.7M solution of t-butyllithium in pentane (10.4 mL, 17.6 mmol). After 15 min add 1-benzyl-1H-indole-2,3-dione (1.90 g, 8 mmol) in ethylene glycol dimethyl ether (32 mL). Remove the bath and allow to warm to room temperature with stirring for 18 h. Quench with saturated NH4Cl solution and extract with ethyl acetate (2×). Wash combined organics with brine and then dry (Na2SO4), filter and concentrate in vacuo to give 3.42 g of a dark purple oil. Purify initially by flash chromatography (25% EtOAC/hexanes) to give 1.20 g of material which by TLC is mostly starting material and product. Purify further by chromatography (step gradient of CH2Cl2, 5% acetonitrile/CH2Cl2, 10% acetonitrile/CH2Cl2) to give 803 mg (22%) of the title compound as a yellow foam. MS (ES): m/z=432 (M+1−H2O); 1H NMR(DMSO-d6); δ7.50-7.18 (m, 12H), 7.00 (m, 2H), 6.95 (s, 2H), 6.77 (s, 1H), 4.93 (q, J=2 Hz, J=18 Hz, 2H), 4.77 (s, 2H), 2.20 (s, 6H).

Workup

  1. customRemove the bath
  2. temperatureto warm to room temperature
  3. customQuench with saturated NH4Cl solution
  4. extractionextract with ethyl acetate (2×)
  5. washWash
  6. dry with materialdry (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-a265d6eb0e8d4467a9c17a82a8bb5b55
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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