Tetrahydrofuran → HCID 59361007, compound

HRID 2059566Notes

Reaction equation

HRID 2059566 reaction equation
[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][CH2:6][C@H:7]1[O:11][CH:10]([O:12][CH3:13])[C:9](=[O:14])[C@@H:8]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24].[CH2:30]1COC[CH2:31]1>>[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][CH2:6][C@H:7]1[O:11][CH:10]([O:12][CH3:13])[C@:9]([C:30]#[CH:31])([OH:14])[C@@H:8]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 58681680HCID 58681680, compound

Product 1

HCID 59361007HCID 59361007, compound

Procedure

To a cold (−20° C.) solution of (4R,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-dihydrofuran-3-one (9.16 g, 19.07 mmol,) in dry THF (20 mL) is added dropwise a solution of 0.5M alkynylmagnesium bromide (e.g. where R3=H, alkynylmagnesium bromide is ethynylmagnesium bromide) in THF (57.2 mL, 28.6 mmol). The yellow reaction mixture is stirred at the same temperature for 1 h and quenched with saturated NH4Cl (50 ml) and extracted with IPAC (2×70 mL). The organic layer is washed with water (50 mL), concentrated to give (3R,4R,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-3-ethynyl-2-methoxy-tetrahydrofuran-3-ol (I-4) (R3=H) as dark red oil which is directly used for the next step.

Workup

  1. customquenched with saturated NH4Cl (50 ml)
  2. extractionextracted with IPAC (2×70 mL)
  3. washThe organic layer is washed with water (50 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e728b83f85e4005b66d269c66240d7d
Source dataset
uspto-grants-2012_10
Patent number
US08278282B2

Reaction notes

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