Diethyl Ether → HCID 18972596, compound

HRID 2395123Notes

Reaction equation

HRID 2395123 reaction equation
[CH2:1]([Li])CCC.[CH2:6]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([CH2:26][CH3:27])[C:14]3[C:19]([O:20][C:21]=2[CH:22]=1)=[CH:18][C:17]([O:23][CH2:24][CH3:25])=[CH:16][CH:15]=3)[CH3:7].[C:28](=[O:31])(O)[O-:29].[Na+].[CH2:33]([O:35][CH2:36]C)[CH3:34]>O1CCCC1>[CH2:26]([N:13]1[C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:6][CH3:7])=[CH:22][C:21]=2[O:20][C:19]2[C:18]([CH2:1][O:29][CH2:28][O:31][CH2:34][CH2:33][O:35][CH3:36])=[C:17]([O:23][CH2:24][CH3:25])[CH:16]=[CH:15][C:14]1=2)[CH3:27]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 18972537HCID 18972537, compoundHCID 178418339Butyllithium

Product 1

HCID 18972596HCID 18972596, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.1 ml of n-butyllithium solution (1.6M in hexane) were added at -78° to a solution of 1.0 g (3.04 mmol) of 3,7-diethoxy-10-ethyl-10H-phenoxazine in 10 ml of absolute tetrahydrofuran. The reaction mixture was stirred at -78° for 30 minutes, brought slowly to 0°, treated with 0.45 ml of 2-(methoxyethoxy)methyl chloride, stirred at room temperature for 2 hours and then poured into ice, saturated sodium bicarbonate solution and diethyl ether. The aqueous phase was extracted twice with diethyl ether and the combined organic phases were dried over magnesium sulphate and evaporated. The residue was chromatographed on 100 g of silica gel with a mixture of diethyl ether/hexane (1:1), whereupon, after drying in a high vacuum, 1.13 g (89%) of 10-ethyl-3,7-diethoxy-4-[[(2-methoxyethoxy)methoxy]methyl]-10H-dibenzo[b,e][1,4]oxazine were obtained as a colourless oil. MS: 417 (M+ ; 100), 388(58), 313(20), 284(44), 254(60), 226(30).

Workup

  1. custombrought slowly to 0°
  2. stirringstirred at room temperature for 2 hours
  3. extractionThe aqueous phase was extracted twice with diethyl ether
  4. dry with materialthe combined organic phases were dried over magnesium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on 100 g of silica gel with a mixture of diethyl ether/hexane (1:1), whereupon
  7. customafter drying in a high vacuum

Sources & evidence

ORD record
ord-60ea2aab26f84b69aeca1c8a9be881a2
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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