Sodium hydride → Benzyl (2e,4s)-4-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-7-methyl-2-octenoate

HRID 1796862Notes

Reaction equation

HRID 1796862 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH:13]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(OP([CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])(OCC)=O)C.[H-].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])/[CH:13]=[CH:28]/[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 281239Benzyl (diethoxyphosphoryl)acetateHCID 87901094(2s)-2-(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)-5-methylhexanal

Product 1

HCID 131725709Benzyl (2e,4s)-4-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-7-methyl-2-octenoate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 8H (2.61 g, 9.16 mmol), benzyl diethylphosphonoacetate (2.83 g, 9.90 mmol), and sodium hydride (0.24 g, 10 mmol) in benzene (40 mL) at room temperature was stirred 2 hours, diluted with ethyl acetate, washed sequentially with saturated aqueous NH4Cl and pH 7 buffer, dried (MgSO4), filtered, and concentrated. Flash column chromatography (silica gel, 2:1 hexanes/CH2Cl2) provided the desired product. MS (ESI) m/e 419 (M+H)+.

Workup

  1. washwashed sequentially with saturated aqueous NH4Cl and pH 7 buffer
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-25c8fb8e2b6d4169a6a94993c662f51b
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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