Triphenylphosphine → Diphenylmethyl 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}-pentanoate

HRID 1604692Notes

Reaction equation

HRID 1604692 reaction equation
[OH:1][CH2:2][C:3]1[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=1[O:5][CH:6]([CH2:23][CH2:24][CH3:25])[C:7]([O:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[C:30]([C:34]1[N:35]=[C:36]([C:39]2[O:40][C:41]3[CH:47]=[CH:46][C:45](O)=[CH:44][C:42]=3[CH:43]=2)[S:37][CH:38]=1)([CH3:33])([CH3:32])[CH3:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:30]([C:34]1[N:35]=[C:36]([C:39]2[O:40][C:41]3[CH:47]=[CH:46][C:45]([O:1][CH2:2][C:3]4[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=4[O:5][CH:6]([CH2:23][CH2:24][CH3:25])[C:7]([O:9][CH:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[O:8])=[CH:44][C:42]=3[CH:43]=2)[S:37][CH:38]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 108586652-(4-Tert-butylthiazol-2-yl)-5-hydroxybenzofuranHCID 19603743HCID 19603743, compound

Product 1

HCID 19603769Diphenylmethyl 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}-pentanoateYield 76.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diphenylmethyl 2-[2-(hydroxymethyl)phenoxy]pentanoate (1.70 g), 2-(4-tert-butylthiazol-2-yl)-5-hydroxybenzofuran (2.43 g), and triphenylphosphine (2.44 g) in tetrahydrofuran (40 ml) was added a solution of diethylazodicarboxylate (1.44 g) in tetrahydrofuran (2 ml) under ice-cooling. The mixture was stirred at the same temperature for an hour and at room temperature for an hour. The mixture was concentrated under reduced pressure and the residue was subjected to a column of silica gel (100 g) eluting with a mixed solvent of toluene and n-hexane (7:3) to give diphenylmethyl 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}phenoxy}pentanate (2.16 g).

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated under reduced pressure
  3. washeluting with a mixed solvent of toluene and n-hexane (7:3)

Sources & evidence

ORD record
ord-c8c2b7bd378b4433ba230273e0f1771b
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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