HCID 178504487, compound → HCID 86671290, compound

HRID 446647Notes

Reaction equation

HRID 446647 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:13](C(C)(C)C)[O:14][SiH](C)C)[CH:6]=[C:7]([C:9]([SH:12])([CH3:11])[CH3:10])[CH:8]=1>C(O)(=O)C.C1COCC1.O>[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([SH:12])([CH3:10])[CH3:11])[CH:6]=[C:5]([CH2:13][OH:14])[CH:4]=1

Participants

3

Reactant 1

HCID 178504487HCID 178504487, compound

Product 1

HCID 86671290HCID 86671290, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

A solution of 43 mg of 5-hydroxymethyl-1-(1-mercapto-1-methylethyl)-3-[(tert-butyl)dimethylsilanyloxymethyl]benzene in 1 ml of an acetic acid/THF/water (3/1/1) mixture is stirred at AT for 4.5 h and concentrated under RP, and then the residue is taken up in 3 ml of water. The pH of the aqueous phase is brought to 7 by addition of a 10% aqueous Na2CO3 solution and then the aqueous phase is extracted with AcOEt. The organic phase is dried over MgSO4 and concentrated under RP. 18 mg of 3,5-bis(hydroxymethyl)-1-(1-mercapto-1-methylethyl)benzene are thus obtained.

Workup

  1. concentrationconcentrated under RP
  2. additionThe pH of the aqueous phase is brought to 7 by addition of a 10% aqueous Na2CO3 solution
  3. extractionthe aqueous phase is extracted with AcOEt
  4. dry with materialThe organic phase is dried over MgSO4
  5. concentrationconcentrated under RP

Sources & evidence

ORD record
ord-844804550b7e47b89fbc7ea91d149f1d
Source dataset
uspto-grants-2013_07
Patent number
US08481042B2

Reaction notes

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