Benzyl Alcohol → HCID 86706096, compound

HRID 2176256Notes

Reaction equation

HRID 2176256 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([OH:9])=[O:8])[CH2:2]1.C(Cl)(=O)C(Cl)=O.[CH2:16](O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl.CN(C)C=O>[CH2:16]([O:8][C:7]([CH:3]1[CH2:4][CH2:5][CH2:6][O:1][CH2:2]1)=[O:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 65578Oxalyl chlorideHCID 16767361Oxane-3-carboxylic acid

Product 1

HCID 86706096HCID 86706096, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A cooled (0° C.) solution of tetrahydro-pyran-3-carboxylic acid (2.831 g, 21.752 mmol) in dichloromethane (60 mL) and N,N-dimethylformamide (5 drops) was treated with oxalyl chloride (2.0 mL, 23.927 mmol). After stirring at room temperature for 2 h, benzyl alcohol (2.5 mL, 23.927 mmol) was added. After stirring at room temperature for 2 h and standing overnight, the volatiles were removed in vacuo and the residue was purified by silica gel chromatography using a 50 g Isolute cartridge eluted with a continuous gradient of iso-hexanes/ethyl acetate 1:0 to 4:1 to afford the title compound (4.587 g, 96%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.58-1.88 (m, 3H), 2.03-2.13 (m, 1H), 2.62-2.72 (m, 1H), 3.47 (ddd, J=11.4, 9.6, 3.4 Hz, 1H), 3.63 (dd, J=11.4, 9.1 Hz, 1H), 3.85 (app dt, J=11.1, 3.8 Hz, 1H), 4.06 (ddd, J=11.4, 4.0, 1.6 Hz, 1H), 5.12, 5.17 (ABq, JAB=12.5 Hz, 2H), 7.31-7.46 (m, 5H).

Workup

  1. stirringAfter stirring at room temperature for 2 h
  2. waitstanding overnight
  3. customthe volatiles were removed in vacuo
  4. customthe residue was purified by silica gel chromatography
  5. washeluted with a continuous gradient of iso-hexanes/ethyl acetate 1:0 to 4:1

Sources & evidence

ORD record
ord-5ed2c8eab1ae477986081b4685da6260
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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