2-Bromoethanol → HCID 18772255, compound

HRID 479639Notes

Reaction equation

HRID 479639 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1.[Br:17][CH2:18][CH2:19]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[Br:17][CH2:18][CH2:19][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11085381Ethyl 7-hydroxychromane-2-carboxylate

Product 1

HCID 18772255HCID 18772255, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 60 ml dichloromethane solution of ethyl 7-hydroxychromane-2-carboxylate (1.32 g, 5.9 mmol), 2-bromoethanol (0.84 ml, 11.9 mmol), and triphenylphosphine (3.12 g, 11.9 mmol) was added diisopropyl azodicarboxylate (2.34 ml, 11.9 mmol) dropwise upon cooling in an ice-water bath. After stirring at rt overnight, the solvent was removed under reduced pressure, and the residue was chromatographed on silica gel eluting with 10% AcOEt/hexanes to give the title compound 1.27 g (65%).

Workup

  1. temperatureupon cooling in an ice-water bath
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was chromatographed on silica gel eluting with 10% AcOEt/hexanes

Sources & evidence

ORD record
ord-17da8f6b1cf44914bff93a28d7124d5d
Source dataset
uspto-grants-2003_11
Patent number
US06645997B2

Reaction notes

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