Cesium carbonate → (1R,2R,4aS,8aS)-1-{[(3,5-dimethoxyphenyl)-sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

HRID 422134

Reaction equation

HRID 422134 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CS(O[CH2:17][C@@H:18]1[C@:27]2([CH3:28])[C@H:22]([C:23]([CH3:30])([CH3:29])[CH2:24][CH2:25][CH2:26]2)[CH2:21][CH2:20][C@:19]1([OH:32])[CH3:31])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([S:11][CH2:17][C@@H:18]2[C@:27]3([CH3:28])[C@H:22]([C:23]([CH3:30])([CH3:29])[CH2:24][CH2:25][CH2:26]3)[CH2:21][CH2:20][C@@:19]2([CH3:31])[OH:32])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 47131453,5-DimethoxybenzenethiolHCID 58294786((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl methanesulfonate

Product 1

HCID 58294829(1R,2R,4aS,8aS)-1-{[(3,5-dimethoxyphenyl)-sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-olYield 60.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3,5-dimethoxybenzenethiol (20) (6.74 g, 39.60 mmol), ((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl methanesulfonate (12) (12.62 g, 39.60 mmol), and Cs2CO3 (38.70 g, 118.77 mmol) in CH3CN (560 mL) was stirred at room temperature for 1 h, then refluxed for 24 h. After cooling, the mixture was concentrated. Purification by chromatography on silica gel (Hexanes/EtOAc, 4:1) gave (1R,2R,4aS,8aS)-1-{[(3,5-dimethoxyphenyl)-sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (21) (9.40 g, 60%) as a light yellow sticky mass.

Workup

  1. temperaturerefluxed for 24 h
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. customPurification by chromatography on silica gel (Hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-fad6eb8251a44e208bce1c76fa01a9cd
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Linked notes

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