1,2-Dichloroethane → 1058129-65-9

HRID 2193010Notes

Reaction equation

HRID 2193010 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.C(Cl)CCl.CCN(CC)CC.[CH3:21][C:22](O)([CH3:24])[CH3:23]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][C:22]([CH3:24])([CH3:23])[CH3:21])=[O:8])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6386tert-ButanolHCID 8471TriethylamineHCID 219302Oxane-4-carboxylic acid

Product 1

HCID 231316161058129-65-9

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

Tetrahydro-2H-pyran-4-carboxylic acid (10 g, 77 mmol) and EDC (17.68 g, 92 mmol) were added to a flask, followed by DCM (200 ml). To the resulting suspension was added Et3N (16 ml, 115 mmol), tBuOH (16.1 ml, 169 mmol) and DMAP (9.39 g, 77 mmol). The reaction mixture was stirred at 40° C. for 18 hr. The reaction mixture was diluted with DCM (100 Ml) and washed with 1N NaOH (1×100 Ml) followed by 1M citric acid solution (1×100 Ml). The organic layer was dried over sodium sulfate, filtered and concentrated to afford tert-butyl tetrahydro-2H-pyran-4-carboxylate. 1H NMR (500 MHz, CDCl3) δ 3.90 (dt, 2H), 3.37 (dt, 2H), 2.38 (septet, 1H), 1.77-1.67 (m, 4H), 1.40 (s, 9H).

Workup

  1. washwashed with 1N NaOH (1×100 Ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5a5f93903b1f4fc0ad07207ac56c3583
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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