Triphenylphosphine → ethyl 5-(4-Boc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate

HRID 606581

Reaction equation

HRID 606581 reaction equation
C1(P([C:14]2[CH:19]=[CH:18]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:34][C:35]1[CH:36]=[CH:37][C:38]2[O:42][C:41]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:40][C:39]=2[CH:48]=1.[C:49]([N:56]1CC[O:59][CH2:58][CH:57]1C(O)=O)([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50]>ClCCl>[C:49]([N:56]1[CH2:57][CH2:58][O:59][CH:19]([CH2:14][O:34][C:35]2[CH:36]=[CH:37][C:38]3[O:42][C:41]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:40][C:39]=3[CH:48]=2)[CH2:18]1)([O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:50]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27601334-(tert-Butoxycarbonyl)morpholine-3-carboxylic acidHCID 22228632Ethyl 5-hydroxybenzofuran-2-carboxylate

Product 1

HCID 67046596ethyl 5-(4-Boc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenyl phosphine polymer bound (8.96 mmol) was suspended in anhydrous dichloromethane (20 ml) then diisopropyl azodicarboxylate (7.76 mmol) was added and the mixture was stirred for 15 minutes at room temperature. Then ethyl 5-hydroxybenzofuran carboxylate (5.97 mmol) was added over 5 minutes followed by the addition of 4-N-boc-3-morpholinecarboxylic acid (5.97 mmol) over 5 minutes too. The mixture was stirred at room temperature over night. The solvent was evaporated under vacuo and the residue purified by flash chromatography to obtain ethyl 5-(4-Boc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate: m/z=406 in MS ES+, as clear oil.

Workup

  1. stirringThe mixture was stirred at room temperature over night
  2. customThe solvent was evaporated under vacuo
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-7ebb8d9bffd14e4a8362df707733df37
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Linked notes

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