Triphenylphosphine → 6-[1-(1H-imidazol-1-ylmethyl)propoxy]-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone

HRID 496440Notes

Reaction equation

HRID 496440 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[C:15]([CH2:25][S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[CH2:19][CH2:18][CH2:17]2.[N:35]1([CH2:40][CH:41](O)[CH2:42][CH3:43])[CH:39]=[CH:38][N:37]=[CH:36]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[N:35]1([CH2:40][CH:41]([O:13][C:14]2[C:15]([CH2:25][S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])=[C:16]3[C:21](=[CH:22][CH:23]=2)[C:20](=[O:24])[CH2:19][CH2:18][CH2:17]3)[CH2:42][CH3:43])[CH:39]=[CH:38][N:37]=[CH:36]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 223247586-hydroxy-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenoneHCID 223247611-(1H-imidazol-1-yl)-2-butanol

Product 1

HCID 223248546-[1-(1H-imidazol-1-ylmethyl)propoxy]-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenoneYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.16 mL, 0.99 mmol) was added over 10 min to a mixture of 6-hydroxy-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone (300 mg, 0.99 mmol), 1-(1H-imidazol-1-yl)-2-butanol (165 mg, 1.08 mmol), triphenylphosphine (260 mg, 0.99 mmol) and tetrahydrofuran (2 mL) under nitrogen. The resulting mixture was stirred for 6 d, whereupon it was concentrated. The residue was purified by dry-flash column chromatography (SiO2, 1-9% 2-propanol-dichloromethane) to give 6-[1-(1H-imidazol-1-ylmethyl)propoxy]-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone as a foam, 125 mg, 29% yield. NMR spectrum was consistent with structure. MS EI: M+• 438.1608 (M+• 438.1613).

Workup

  1. concentrationwas concentrated
  2. customThe residue was purified by dry-flash column chromatography (SiO2, 1-9% 2-propanol-dichloromethane)

Sources & evidence

ORD record
ord-ff972102633b436ab5de739c8055a17f
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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