HCID 15414663, compound → HCID 178521440, compound

HRID 2396420Notes

Reaction equation

HRID 2396420 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13]>COC(OC)(C)C>[CH2-:10][C:11]([CH3:12])=[O:14].[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13]

Participants

3

Reactant 1

HCID 15414663HCID 15414663, compound

Product 1

HCID 178521440HCID 178521440, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

11-Bromoundecan-1,2-diol (2.65 g) was dissolved in 2,2-dimethoxypropane (10 mL) and acetone (20 mL) which had been dried over anhydrous K2CO3 for 1 hour. Toluene sulfonic acid (0.18 g) was added and the reaction stirred at room temperature for 19 hours. Solid K2CO3 was added and the mixture was stirred for 30 minutes. The solid was filtered off and the solvent evaporated. The product (11-bromoundecan-1,2-diol acetonide) was isolated in 79% yield (2.42 g) by flash chromatography on Sio2 with CH2Cl2.

Workup

  1. dry with materialacetone (20 mL) which had been dried over anhydrous K2CO3 for 1 hour
  2. additionToluene sulfonic acid (0.18 g) was added
  3. additionSolid K2CO3 was added
  4. stirringthe mixture was stirred for 30 minutes
  5. filtrationThe solid was filtered off
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-3ffcb481bc5c435d9f594e847cc79210
Source dataset
uspto-grants-1996_02
Patent number
US05492803

Reaction notes

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