Sodium hydride → HCID 69472984, compound

HRID 1180453Notes

Reaction equation

HRID 1180453 reaction equation
C([Si](C(C)C)(C(C)C)[SH:5])(C)C.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)O)=[CH:15][CH:14]=1.[H-].[Na+].Br[CH:30]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:31]([O:33][CH3:34])=[O:32].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C.O1CCCC1.C(OCC)C>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:5][CH:30]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:31]([O:33][CH3:34])=[O:32])=[CH:15][CH:14]=1

Participants

9

Reactant 5

HCID 24758Sodium hydrideHCID 98221p-Bromobenzhydryl alcoholHCID 2724141Tetrabutylammonium FluorideHCID 3435097Tris(propan-2-yl)silanethiolHCID 12957039Methyl 2-bromo-4-methylpentanoate

Product 1

HCID 69472984HCID 69472984, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triisopropylsilanethiol (1.75 mL, 8.05 mmoles) and (4-bromophenyl)(phenyl)methanol from example 67 step 2 (3.5, 8.05 mmoles) in 16 mL of DMF was added sodium hydride as a 60% emulsion in oil (386 mg, 9.66 mmoles). After the exotherm has passed, 1.65 mL (10 mmole) of methyl 2-bromo-4-methylpentanoate was added followed by 12 mL of a 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran. After stirring overnight, the reaction was diluted with diethyl ether (200 mL) and washed twice with 0.1 N HCl, twice with water and once with brine. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The oil as purified by flash chromatography (9:1 hexanes to ethyl acetate) to give the title ester.

Workup

  1. washwashed twice with 0.1 N HCl, twice with water and once with brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe oil as purified by flash chromatography (9:1 hexanes to ethyl acetate)

Sources & evidence

ORD record
ord-f6df932610b54633821b6bc84ebf20a9
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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