1,5-Pentanediol → HCID 19894604, compound

HRID 266237Notes

Reaction equation

HRID 266237 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[OH:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][O:7][S:16]([CH3:15])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 81051,5-PentanediolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 19894604HCID 19894604, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a solution of 85.0 g (0.904 mole) of 1,5-pentanediol and 30.3 g (0.30 mole) of triethylamine in 350 mL of dry CH2Cl2 at -20° C. was added dropwise a solution of 28.5 g (0.25 mole) of methanesulfonylchloride in 100 mL of CH2Cl2 over 2 hours under nitrogen atmosphere. The solution was stirred at 2 hours at -20° C. and then at -4° C. for 18 hours. The reaction mixture was washed with H2O, 1N HCl, H2O, then dried and evaporated. The residual oil was chromatographed on a silica gel column, eluting with EtOAc-CH2Cl2 (2:8). After combining the appropriate fractions there was obtained 25.7 g (56.5%) of 5-hydroxypentylmethylsulfonate as a colorless oil.

Workup

  1. waitat -4° C. for 18 hours
  2. washThe reaction mixture was washed with H2O, 1N HCl, H2O
  3. customdried
  4. customevaporated
  5. customThe residual oil was chromatographed on a silica gel column
  6. washeluting with EtOAc-CH2Cl2 (2:8)

Sources & evidence

ORD record
ord-1747e0fc1dc949859cbb71bec852dbfb
Source dataset
uspto-grants-1997_07
Patent number
US05650510

Reaction notes

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