Triethylamine → Ethyl 4-(hydroxymethyl)oxane-4-carboxylate

HRID 49041Notes

Reaction equation

HRID 49041 reaction equation
CS(Cl)(=O)=O.CS([O:10][CH2:11][C:12]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)(=O)=O.C(N(CC)CC)C>ClCCl>[OH:10][CH2:11][C:12]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 20635576Ethyl 4-(Methanesulfonyloxy)methyltetrahydropyran-4-carboxylate Methanesulfonyl chloride

Product 1

HCID 22439651Ethyl 4-(hydroxymethyl)oxane-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 3 Ethyl 4-(Methanesulfonyloxy)methyltetrahydropyran-4-carboxylate Methanesulfonyl chloride (4.6 ml) was added to a solution of intermediate 2 (1 1.0 g) at 0° C. in dichloromethane (30 ml), followed by triethylamine (8.0 ml). The mixture was stirred for 1 h, then washed with citric acid (5% aq, 30 ml), saturated sodium bicarbonate and brine. The organic layer was separated, and then dried (MgSO4) and evaporated to give the title compound as colourless oil (15.2 g).

Workup

  1. washwashed with citric acid (5% aq, 30 ml), saturated sodium bicarbonate and brine
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-ccfd5a096bc148778ce85d66afde09e6
Source dataset
uspto-grants-2004_03
Patent number
US06706719B1

Reaction notes

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