Iodoethane → HCID 59226841, compound

HRID 659903Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:35]=[CH:34][C:11]([CH2:12][C:13]2[CH:20]=[C:19]([C@@:21]34[O:28][C@@:25]([CH2:29][OH:30])([CH2:26][O:27]3)[C@@H:24]([OH:31])[C@H:23]([OH:32])[C@H:22]4[OH:33])[CH:18]=[CH:17][C:14]=2[C:15]#[N:16])=[CH:10][CH:9]=1.I[CH2:37][CH3:38]>CC(C)=O.C(OCC)(=O)C>[CH2:37]([O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][C:13]2[CH:20]=[C:19]([C@@:21]34[O:28][C@@:25]([CH2:29][OH:30])([CH2:26][O:27]3)[C@@H:24]([OH:31])[C@H:23]([OH:32])[C@H:22]4[OH:33])[CH:18]=[CH:17][C:14]=2[C:15]#[N:16])=[CH:34][CH:35]=1)[CH3:38]

Participants

Conditions

Temperature: 45 °C

Procedure

Potassium carbonate (8 mg, 0.058 mmol) was added to a solution of intermediate 2-(4-hydroxy-benzyl)-4-((1S,2S,3S,4R,5S)-2,3,4-trihydroxy-1-hydroxymethyl-6,8-dioxa-bicyclo[3.2.1]oct-5-yl)-benzonitrile (see example 6; 8.9 mg, 0.022 mmol) in acetone (0.4 mL), followed by iodoethane (4 microL, 0.044 mmol) at room temperature. The mixture was stirred at 45° C. overnight. The mixture was diluted with ethyl acetate (60 mL) and washed with water. The organic layer was dried over sodium sulfate and evaporated to dryness. Purification by preparative Thin Layer Chromatography over silica gel (eluting with methanol in dichloromethane: 1 to 9 in volume) allowed isolation of desired product 7A (2.4 mg; 26% yield).

Workup

washwashed with water
dry with materialThe organic layer was dried over sodium sulfate
customevaporated to dryness
customPurification by preparative Thin Layer Chromatography over silica gel (eluting with methanol in dichloromethane: 1 to 9 in volume)

Sources & evidence

ORD record: ord-c233f1e6841443f2853a69481dea56ed
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080580B2

Reaction notes

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