Sodium hydride → HCID 86739928, compound

HRID 1284878Notes

Reaction equation

HRID 1284878 reaction equation
Cl[C:2]([CH2:7][C:8]([F:33])([F:32])[CH2:9][C@H:10]([C@@H:12]1[C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19]([CH2:20][C@@H:21]([OH:31])[CH2:22][CH2:23]2)=[CH:18][CH2:17]3)[CH2:14][CH2:13]1)[CH3:11])([CH2:5][OH:6])[CH2:3][OH:4].[H-].[Na+]>C(COC)OC>[O:4]1[CH2:3][C:2]1([CH2:7][C:8]([F:33])([F:32])[CH2:9][C@H:10]([C@@H:12]1[C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19]([CH2:20][C@@H:21]([OH:31])[CH2:22][CH2:23]2)=[CH:18][CH2:17]3)[CH2:14][CH2:13]1)[CH3:11])[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 57027331HCID 57027331, compound

Product 1

HCID 86739928HCID 86739928, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The chlorodiol (11) (183 mg, 0.32 mmol) was treated with sodium hydride (18 mg, 0.75 mmol) in dimethoxyethane (18 ml) at room temperature for 6 days. The usual work-up (ether for extraction) gave a crude product, which was applied to a column of silica gel (100 g). Elution with dichloromethane provided the epoxyalcohol (12) (56 mg, 32%), glass. 1H-NMr δ: 2.92 (2H, m, 26-H2), 3.67-4.16 (3H, m, 3-H and 27-H2). MS m/z: 434 (M+ -THP OH), 416, 404, and the recovery of chlorodiol 11 (92 mg, 50%).

Workup

  1. extractionThe usual work-up (ether for extraction)
  2. customgave a crude product, which
  3. washElution with dichloromethane

Sources & evidence

ORD record
ord-dce16cfea4514ec9b79584e594f847a7
Source dataset
uspto-grants-1986_01
Patent number
US04564474

Reaction notes

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