Diethyl Ether → HCID 131726817, compound

HRID 899618Notes

Reaction equation

HRID 899618 reaction equation
[C@@H:1]1(CO)[CH2:3][C@H:2]1[CH2:4][OH:5].[H-].[Na+].[C:10]([Si:14](C)(C)Cl)([CH3:13])([CH3:12])[CH3:11].C([O:20][CH2:21][CH3:22])C.[CH2:23]1COCC1>>[OH:5][CH2:4][C@@H:2]1[CH2:3][C@H:1]1[C:21]([CH3:22])([CH3:23])[O:20][SiH2:14][C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 111159962345-75-7

Product 1

HCID 131726817HCID 131726817, compoundYield 65%

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) stirred solution of trans-1,2-cyclopropanedimethanol (2.0 g, 20 mmol) in THF (40 mL) was slowly added NaH (60% dispersion in oil, 0.80 g, 20 mmol). Stirring was continued at 0° C. for 10 min. tert-Butyldimethylchlorosilane (3.0 g, 20 mmol) was added. The thick white slurry was allowed to warm to room temperature and stirring was continued for 10 min. The resultant mixture was poured into diethyl ether (400 mL) and washed with 10% K2CO3 (100 mL) then washed again with brine (100 mL). The separated organic layer was dried over Na2SO4 and concentrated. The crude material was purified by flash column chromatography (5 cm id., 100 g silica gel, eluted with 5:1 hexanes/ethyl acetate) to give the mono-protected desired product as a clear oil (2.8 g, 65%). 1H NMR (CDCl3) δ 0.05 (s, 6H), 0.41-0.53 (m, 2H), 0.89 (s, 9H), 0.89-1.04 (m, 2H), 1.41 (t, 1H, J=5.8 Hz), 3.41-3.50 (m, 3H), 3.60 (dd, 1H, J=11.2, 5.8 Hz).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirring
  3. waitwas continued for 10 min
  4. washwashed with 10% K2CO3 (100 mL)
  5. washthen washed again with brine (100 mL)
  6. dry with materialThe separated organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude material was purified by flash column chromatography (5 cm id., 100 g silica gel, eluted with 5:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-58e3d5c33e964376b0a047555589a779
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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