Triphenylphosphine → Ethyl 2-[(6-bromo-1-methyl-2-naphthyl)oxy]-3-phenylpropanoate

HRID 1359227Notes

Reaction equation

HRID 1359227 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:12])=[C:7]([OH:13])[CH:6]=[CH:5]2.O[CH:15]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17].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>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:12])=[C:7]([O:13][CH:15]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 279772-Naphthol, 6-bromo-1-methyl-HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 6429708Ethyl phenyllactate, (+-)-

Product 1

HCID 18182806Ethyl 2-[(6-bromo-1-methyl-2-naphthyl)oxy]-3-phenylpropanoateYield 43.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Following the procedure described in Step 2 of Example 4, 6-bromo-1-methyl-2-naphthol (2.44 g 10.3 mmol) was coupled to ethyl 2-hydroxy-3-phenylpropanoate (3.0 g, 15 mmol) in presence of triphenylphosphine (4.17 g, 15.9 mmol) and diisopropyl azodicarboxylate (3.0 mL, 15 mmol) in benzene (65 mL). Purification by flash chromatography using 100% hexane and 1-4% ethyl acetate in hexane as eluants afforded ethyl 2-[(6-bromo-1-methyl-2-naphthyl)oxy]-3-phenylpropanoate as a transparent yellow gum (1.86 g). 1HNMR (400 MHz, DMSO-d6): δ8.1 (s, 1H), 7.9 (d, 1H, J=7.0 Hz), 7.7 (d, 1H, J=7.0 Hz), 7.6 (d, 1H, J=6.3 Hz), 7.3-7.4 (m, 4 H), 7.2-7.3 (m, 2H), 5.25 (t, 1H, J=6.3 Hz), 4.1 (q, 2H, J=7.0 Hz), 3.25-3.35 (m, 2H), 2.45 (s, 3H), and 1.1 ppm (t, 3H, J=7.0 Hz).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-ff68eb540295489390a1de91d80ba12c
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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