2-Bromoethanol → HCID 23438473, compound

HRID 2120090Notes

Reaction equation

HRID 2120090 reaction equation
[CH:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]4[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=4)[N:13]=3)=[C:10]([CH3:26])[O:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:58][CH2:59][CH2:60]O>C1COCC1>[Br:58][CH2:59][CH2:60][O:25][C:21]1[CH:20]=[C:19]([NH:18][C:14]2[N:13]=[C:12]([C:11]3[C:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[N:8][O:9][C:10]=3[CH3:26])[CH:17]=[CH:16][N:15]=2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23438475HCID 23438475, compound

Product 1

HCID 23438473HCID 23438473, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of phenol 11 (880 mg, 2.51 mmol) in THF (anhydrous, 5 ml) was added diethyl azodicarboxylate (0.52 ml, 3.27 mmol) and triphenylphosphine (857 mg, 3.27 mmol) followed by 2-bromoethanol (0.23 ml, 3.27 mmol) at 0° C. The resulting mixture was stirred at room temperature for 4 hours and the solvent was removed in vacuo. The crude product was purified by silica gel chromatography (30% EtOAC:hexanes) to afford the desired bromo derivative 12 (745 mg) as a white solid in 65% yield. 1H NMR (CDCl3) δ 1.2-2.0 (m, 10H), 2.5 (s, 3H), 3.1 (m, 1H), 3.6 (t, 2H), 4.3 (t, 2H), 6.6 (d, 1H), 6.7 (d, 1H), 7.1 (d, 1H), 7.1(s, 1H), 7.3 (dd, 1H), 7.4 (s, 1H), 8.4 (d, 1H)

Workup

  1. customthe solvent was removed in vacuo
  2. customThe crude product was purified by silica gel chromatography (30% EtOAC:hexanes)

Sources & evidence

ORD record
ord-e8401c46f15a4f6a94cc4c8d65898f79
Source dataset
uspto-grants-2004_02
Patent number
US06689778B2

Reaction notes

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