Triphenylphosphine → HCID 67420607, compound

HRID 1423964Notes

Reaction equation

HRID 1423964 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-a621ea07484f41aeb86e33a02ba9d5b6
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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