Water → HCID 22910718, compound

HRID 1378266Notes

Reaction equation

HRID 1378266 reaction equation
[Br:1][CH2:2][CH2:3][CH:4]1OCCO1.[CH:9](/[CH:13]([CH2:16][OH:17])[CH2:14][OH:15])=[CH:10]\[CH2:11][CH3:12].S(=O)(=O)(O)O.O>C1(C)C=CC=CC=1.C(N(CC)CC)C>[Br:1][CH2:2][CH2:3][CH:4]1[O:17][CH2:16][CH:13](/[CH:9]=[CH:10]/[CH2:11][CH3:12])[CH2:14][O:15]1

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 22910724HCID 22910724, compound

Product 1

HCID 22910718HCID 22910718, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 14.4 ml of 2-(2-bromoethyl)-dioxolane and 20.6 g of (E)-2-but-1-enyl-1,3-propanediol in 200 ml of toluene was heated to slight boiling overnight with 2.7 ml of 10% aqueous sulfuric acid (v/v) and 8 ml of water. The mixture was treated with 6 ml of triethylamine and the aqueous phase was separated. The organic phase was washed with semi-conc. sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The resulting orange oil (31.3 g) was chromatographed on 400 g of silica gel with hexane/ethyl acetate 2.5% (v/v). 23.4 g of (E)-2-(2-bromoethyl)-5-but-1-enyl-1,3-dioxane (GC purity 97.5%, trans/cis ratio 73:27) were obtained as a yellowish oil.

Workup

  1. customthe aqueous phase was separated
  2. washThe organic phase was washed with semi-conc
  3. dry with materialsodium chloride solution, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting orange oil (31.3 g) was chromatographed on 400 g of silica gel with hexane/ethyl acetate 2.5% (v/v)

Sources & evidence

ORD record
ord-8a0a03ac9b714e7a8dfd47f22ee8cf0a
Source dataset
uspto-grants-1997_09
Patent number
US05667721

Reaction notes

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