Triethylamine → 3-(2-tert-Butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-[2-(2-hydroxymethyl-thiophen-3-yl)-ethyl]6-isopropyl-5,6-dihydro-pyran-2-one

HRID 23509Notes

Reaction equation

HRID 23509 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH2:11][CH2:12][C:13]2[CH:17]=[CH:16][S:15][C:14]=2[CH2:18][OH:19])([CH:8]([CH3:10])[CH3:9])[O:5][C:4](=[O:20])[CH:3]=1.[C:21]([C:25]1[CH:30]=[C:29]([CH2:31][OH:32])[C:28]([CH3:33])=[CH:27][C:26]=1[S:34]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:24])([CH3:23])[CH3:22].CCN(CC)CC>C(#N)C>[C:21]([C:25]1[CH:30]=[C:29]([CH2:31][OH:32])[C:28]([CH3:33])=[CH:27][C:26]=1[S:34][C:3]1[C:4](=[O:20])[O:5][C:6]([CH2:11][CH2:12][C:13]2[CH:17]=[CH:16][S:15][C:14]=2[CH2:18][OH:19])([CH:8]([CH3:9])[CH3:10])[CH2:7][C:2]=1[OH:1])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10499026S-[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl] 4-methylbenzenesulfonothioateHCID 546900474-Hydroxy-6-[2-(2-hydroxymethyl-thiophen-3-yl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

Product 1

HCID 546770333-(2-tert-Butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-[2-(2-hydroxymethyl-thiophen-3-yl)-ethyl]6-isopropyl-5,6-dihydro-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared as described in General Method 16b using 4-hydroxy-6-[2-(2-hydroxymethyl-thiophen-3-yl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one (Example E-24; 1 mmol), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester (Example BB-2; 1.05 mmol), NEt3 (2.2 mmol) in acetonitrile (5 mL). The product was chromatographed over silica gel using 97.5:2.5 CH2Cl2:MeOH, mp 87-90° C. MS (APCI): 503 (M−H).

Workup

  1. customThe product was chromatographed over silica gel using 97.5:2.5 CH2Cl2

Sources & evidence

ORD record
ord-e4d5d5caa7a64b8aa9e872cc496130f3
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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