4-Toluenesulfonyl chloride → rac-Toluene-4-sulfonic acid (1R*,8R*,9R*)-2-(9-hydroxy-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-yl)-ethyl ester

HRID 1879350Notes

Reaction equation

HRID 1879350 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([OH:16])[CH2:13][CH:12]2[CH2:14][CH2:15][CH:5]1[C:6]1[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=1.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18].CCN(CC)CC>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[OH:16][C@@:4]1([CH2:3][CH2:2][O:1][S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:13][C@H:12]2[CH2:14][CH2:15][C@@H:5]1[C:6]1[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 70999516rac-(1R*,8R*,9R*)-9-(2-Hydroxy-ethyl)-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-ol

Product 1

HCID 87403382rac-Toluene-4-sulfonic acid (1R*,8R*,9R*)-2-(9-hydroxy-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-yl)-ethyl esterYield 79.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2.0 g of rac-(1R*,8R*,9R*)-9-(2-hydroxy-ethyl)-tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-ol, 1.9 g of TsCl, 1.5 mL of NEt3 and 0.22 g of DMAP in 120 mL of toluene was stirred overnight at rt. The reaction mixture was quenched with water, the organic phase was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by CC with Hept/EtOAc (1:1) to yield 2.7 g of the desired compound as yellow oil.

Workup

  1. customThe reaction mixture was quenched with water
  2. customthe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by CC with Hept/EtOAc (1:1)

Sources & evidence

ORD record
ord-52851e5f6fcd4c37b5561171680bd8a2
Source dataset
uspto-grants-2012_11
Patent number
US08314253B2

Reaction notes

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