Tetrahydrofuran → 5-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1-hydroxy-2,2-dimethoxy-1-methylethyl)-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881884Notes

Reaction equation

HRID 1881884 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:14](=[O:17])[CH:15]=[CH2:16])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[OH:25][C:26]([C:33]1[S:37][C:36]([CH:38]=[O:39])=[N:35][CH:34]=1)([CH3:32])[CH:27]([O:30][CH3:31])[O:28][CH3:29].C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:14](=[O:17])[CH2:15][CH2:16][C:38]([C:36]3[S:37][C:33]([C:26]([OH:25])([CH3:32])[CH:27]([O:30][CH3:31])[O:28][CH3:29])=[CH:34][N:35]=3)=[O:39])=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 593312584-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-oneHCID 593315475-(1-Hydroxy-2,2-dimethoxy-1-methylethyl)-1,3-thiazole-2-carbaldehyde

Product 1

HCID 593313885-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1-hydroxy-2,2-dimethoxy-1-methylethyl)-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dioneYield 69%

Reagents, catalysts & solvents 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (1.00 g), 5-(1-hydroxy-2,2-dimethoxy-1-methylethyl)-1,3-thiazole-2-carbaldehyde (0.73 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (77 mg), triethylamine (0.16 mL), tetrahydrofuran (8 mL) and ethanol (8 mL) was stirred with heating under reflux for 2 hr. The reaction mixture was concentrated, and the residue was subjected to basic silica gel column chromatography, and the title compound (1.14 g, yield 69%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio). MS: 580 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hr
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-9160f933f2b0421b9e62006de478173e
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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