Water → 3,5-Bis-o-(2,4-dichlorophenylmethyl)-2-c-ethyl-1-o-methyl-alpha-d-ribofuranose

HRID 2212914Notes

Reaction equation

[CH3:1][CH2:2][Mg+].[Br-].[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH2:13][O:14][C@@H:15]1[C@@H:21]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[O:20][C@H:17]([O:18][CH3:19])[C:16]1=[O:33].O>CCOCC>[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH2:13][O:14][C@@H:15]1[C@@H:21]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[O:20][C@H:17]([O:18][CH3:19])[C@:16]1([CH2:2][CH3:1])[OH:33]

Participants

Conditions

Temperature: -78 °C

Procedure

To diethyl ether (300 mL) at −78° C. was slowly added EtMgBr (3.0 M, 16.6 mL) and then dropwise the compound from Step B of Example 62 (4.80 g, 10.0 mmol) in anhydrous Et2O (100 mL). The reaction mixture was stirred at −78° C. for 15 min, allowed to warm to −15° C. and stirred for another 2 h, and then poured into a stirred mixture of water (300 mL) and Et2O (600 mL). The organic phase was separated, dried (MgSO4), and evaporated in vacuo. The crude product was purified on silica gel using ethyl acetate/hexane (1:2) as eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (3.87 g) as a colorless oil.

Workup

customat −78° C.
temperatureto warm to −15° C.
stirringstirred for another 2 h
customThe organic phase was separated
dry with materialdried (MgSO4)
customevaporated in vacuo
customThe crude product was purified on silica gel
additionFractions containing the product
customevaporated in vacuo

Sources & evidence

ORD record: ord-1d41ba247cf440bb81f3c1b307b65e80
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105499B2

Reaction notes

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