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Acetic Acid → 3-(2-(3-methoxyphenyl)acetyl)dihydro-2H-pyran-4(3H)-one

HRID 1930696
Notes
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Reaction equation

HRID 1930696 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH2:26][C:27](Cl)=[O:28])[CH:23]=[CH:24][CH:25]=1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH2:26][C:27]([CH:3]2[C:4](=[O:7])[CH2:5][CH2:6][O:1][CH2:2]2)=[O:28])[CH:23]=[CH:24][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 27332463-Methoxyphenylacetyl chlorideHCID 2733832Lithium hexamethyldisilazane

Product 1

HCID 593337883-(2-(3-methoxyphenyl)acetyl)dihydro-2H-pyran-4(3H)-oneYield 46.2%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Tetrahydro-4H-pyran-4-one (0.138 mL, 1.50 mmol) was dissolved in toluene (1 mL) and cooled to 0° C. LHMDS (1.573 mL, 1.57 mmol) was added. 3-Methoxyphenylacetyl chloride (0.117 mL, 0.75 mmol) was added after 2 minutes. After 5 minutes, acetic acid (0.129 mL, 2.25 mmol) and water was added. The organic phase was separated and the crude product was purified by flash column chromatography (EtOAc 0-40% in heptane) yielding 3-(2-(3-methoxyphenyl)acetyl)dihydro-2H-pyran-4(3H)-one (86 mg, 46%).

Workup

  1. customThe organic phase was separated
  2. customthe crude product was purified by flash column chromatography (EtOAc 0-40% in heptane)

Sources & evidence

ORD record
ord-6f161a35a68f4b3a839972ed7cc52b1c
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188101B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes