Acetic Acid → 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropyl acetate

HRID 1517873Notes

Reaction equation

HRID 1517873 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1([OH:12])[CH2:11][CH2:10]1.[C:13](O)(=[O:15])[CH3:14].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:13]([O:12][C:9]1([CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH2:10][CH2:11]1)(=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 105591141-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropanol

Product 1

HCID 666697401-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropyl acetateYield 60.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropanol (172 mg, 1 mmol) and acetic acid (120 mg, 2 mmol, Shantou Xilong chemical factory) in 2 mL of DCM was added DMAP (12 mg, 0.1 mmol, aladdin) at rt. After stirring for 30 min, DCC (840 mg, 4 mmol, Aldrich) was added at 0° C. The reaction was quenched with water after all of 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropanol disappeared (monitored by TLC) (about 4 hours). The solid formed during the reaction was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE: EtOAc=20:1) to give the desired compound as yellow oil (130 mg, 60.7%).

Workup

  1. customThe reaction was quenched with water after all of 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropanol
  2. custom(monitored by TLC) (about 4 hours)
  3. customThe solid formed during the reaction
  4. customwas removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (PE: EtOAc=20:1)

Sources & evidence

ORD record
ord-c2466afe4fd5427fa9e0aaba28c1b0af
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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