Triphenylphosphine → HCID 67420607, compound

HRID 1746239Notes

Reaction equation

HRID 1746239 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:24])[S:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][C:11]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:10][CH:9]=2)=[O:4].[C:25]([Si:29]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:30][CH2:31]O)([CH3:28])([CH3:27])[CH3:26].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>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:24])[S:7][C:8]2[C:13]([C:14]=1[O:15][CH2:31][CH2:30][Si:29]([C:25]([CH3:26])([CH3:28])[CH3:27])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[CH:12][C:11]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:10][CH:9]=2)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11312156HCID 11312156, compoundHCID 178498943HCID 178498943, compound

Product 1

HCID 67420607HCID 67420607, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6-benzyloxy-4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester (Compound 62 (h), 591 mg, 1.73 mmol) and 2-(tert-Butyl-diphenyl-silanyl)-ethanol (687 mg, 2.42 mmol) (prepared according to the procedure published in J. Org. Chem. 2005, 70(4), 1467-1470) in THF (7 mL) was added triphenylphosphine (634 mg, 2.42 mmol), and DIAD (489 mg, 2.42 mmol). The resultant mixture was stirred at rt for 3.5 h. After concentration, the crude residue was purified by silica gel chromatography (eluting with 0-75% EtOAc/hexanes) to provide the title compound (697 mg). 1H NMR (200 MHz, CDCl3): δ (ppm)=7.69-7.14 (m, 18H), 5.83 (s, 2H), 4.25-4.09 (m, 2H), 3.49 (s, 3H), 1.89-1.81 (m, 2H), 1.08 (s, 9H).

Workup

  1. customprepared
  2. concentrationAfter concentration
  3. customthe crude residue was purified by silica gel chromatography (eluting with 0-75% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b74d33e3c5184591acfb8b5d95487955
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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