Water → HCID 54273379, compound

HRID 1384729Notes

Reaction equation

HRID 1384729 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[CH2:2][OH:3].C(N(C(C)C)CC)(C)C.[Si:22](OS(C(F)(F)F)(=O)=O)([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24].O>C(Cl)Cl>[CH2:6]([O:5][C:1](=[O:4])[CH2:2][O:3][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 561337Benzyl 2-hydroxyacetateHCID 2724529Triisopropylsilyl trifluoromethanesulfonate

Product 1

HCID 54273379HCID 54273379, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzyl glycolate (46.91 g, 0.282 mol) and diisopropylethylamine (74 mLs, 0.423 mol) in CH2Cl2, cooled via water bath, was added a solution of TIPSOTf (95 g, 0.31 mol) in CH2Cl2. The resulting mixture was allowed to warm to ambient temperature then poured into water, washed twice with 10% aqueous NaHSO4, dried over Na2SO4 and concentrated in vacuo. Flash chromatography (SiO2, 0 to 5% EtOAc in hexanes) afforded 71.6 g of 663.

Workup

  1. washwashed twice with 10% aqueous NaHSO4
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfc301a9d95c472fb3a2688a69bee6e6
Source dataset
uspto-grants-2001_07
Patent number
US06258948B1

Reaction notes

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