Thionyl Chloride → HCID 88608963, compound

HRID 2166297Notes

Reaction equation

HRID 2166297 reaction equation
[CH2:1]([O:3][P:4]([O:40][CH2:41][CH3:42])([C:6]([F:39])([F:38])[C:7]1([O:28][C@H:27]([CH2:29][O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:9]1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)O)=[O:5])[CH3:2].S(Cl)([Cl:45])=O>ClCCl.CN(C)C=O.CCOCC>[CH2:1]([O:3][P:4]([O:40][CH2:41][CH3:42])([C:6]([F:39])([F:38])[C:7]1([Cl:45])[O:28][C@H:27]([CH2:29][O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:9]1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 88609167HCID 88609167, compound

Product 1

HCID 88608963HCID 88608963, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 14.4 g of 1-deoxy-1-(diethoxyphosphinyl)-1,1-difluoro-3,4,6-tris-O-(phenylmethyl)-D-fructofuranose in 50 ml of dichloromethane was added 7.3 ml of thionyl chloride and several drops of dimethylformamide. The solution was stirred at 25° C. for 16 hours, then diluted with ether and treated with icewater. The ether layer was washed with sodium bicarbonate solution, water and brine, dried and concentrated. The residue was subjected to column chromatography on silica gel, giving the desired compound as an oil, CMR δ 105.1 (multiplet, anomeric carbon atom).

Workup

  1. additiontreated with icewater
  2. washThe ether layer was washed with sodium bicarbonate solution, water and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ebb30592325d4f759a3c3c1c7bc3cb18
Source dataset
uspto-grants-1990_07
Patent number
US04943629

Reaction notes

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