Triphenylphosphine → HCID 57438392, compound

HRID 1161119Notes

Reaction equation

HRID 1161119 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[I:34][C:35]1[CH:36]=[C:37]([CH2:41][OH:42])[CH:38]=[CH:39][CH:40]=1.[Cl:43][C:44]1[C:45]([OH:54])=[C:46]([C:51](=[O:53])[CH3:52])[CH:47]=[CH:48][C:49]=1O>ClCCl.O1CCCC1>[Cl:43][C:44]1[C:45]([OH:54])=[C:46]([C:51](=[O:53])[CH3:52])[CH:47]=[CH:48][C:49]=1[O:42][CH2:41][C:37]1[CH:38]=[CH:39][CH:40]=[C:35]([I:34])[CH:36]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 423003-Iodobenzyl alcoholHCID 5363146Diisopropyl azodicarboxylateHCID 574382941-(3-Chloro-2,4-dihydroxy-phenyl)ethanone

Product 1

HCID 57438392HCID 57438392, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add triphenylphosphine (13.6 g, 51.7 mmol) and DIAD (10.5 g, 51.7 mmol) to a solution of (3-iodo-phenyl)-methanol (11.0 g, 47.0 mmol) and 1-(3-Chloro-2,4-dihydroxy-phenyl)-ethanone (8.77 g, 47.0 mmol) in dichloromethane:tetrahydrofuran (250 ml:250 ml) and stir. After 18 hours, concentrate the reaction, and load directly onto silica. Purify the residue by flash chromatography eluting with acetone:hexanes to yield the title product as a white solid (12.2 g, 64%): 1H NMR (DMSO-d6) δ 2.62 (s, 3H), 5.34 (s, 2H), 6.88 (d, 1H), 7.23 (t, 1H), 7.48 (d, 1H), 7.72 (d, 1H), 7.87 (s, 1H), 7.96 (d, 1H), 13.14 (s, 1H).

Workup

  1. concentrationconcentrate
  2. customthe reaction, and load directly onto silica
  3. customPurify the residue by flash chromatography
  4. washeluting with acetone

Sources & evidence

ORD record
ord-f0a3dc7b3e7a4ff980f6d097a831eb92
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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