Triethylamine → HCID 25171020, compound

HRID 416680Notes

Reaction equation

HRID 416680 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:10]=[C:11]([CH:14]([CH3:16])[CH3:15])[CH:12]=[O:13].C1(P(C2C=CC=CC=2)[C@@H]([C@H](P(C2C=CC=CC=2)C2C=CC=CC=2)C)C)C=CC=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Rh].[Rh].[Rh].[Rh]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:10][CH:11]([CH:14]([CH3:16])[CH3:15])[CH:12]=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2724948(R,R)-ChiraphosHCID 87079984HCID 87079984, compound

Product 1

HCID 25171020HCID 25171020, compound

Reagents, catalysts & solvents 2

HCID 994031219584-30-6Catalyst2×HCID 1140TolueneSolvent

Procedure

A solution of 2-(3-(methoxypropoxy)-4-methoxybenzylidene) -3-methylbutanal (7.0 mmol, 74% E and 26% Z), tetrarhodium dodecacabonyl (0.14 mmol), (2R,3R)-(+)-2,3-Bis-(Diphenylphosphino)butane (R, R-Chiraphos, 0.63 mmol) and 300 ul triethylamine in toluene (75 ml) was transferred into an autoclave. The mixture was hydrogenated at 70-80° C. and 20 bar H2. After 42 hr additional tetrarhodium dodecacarbonyl (0.14 mmol) was added to complete the reaction in 62 hr. The mixture was concentrated to 3.5 g black oil and purified by flash chromatography (heptane/ethyl acetate=2/1). Yield=1.6 g yellow oil (74%).

Workup

  1. customwas hydrogenated at 70-80° C.
  2. customthe reaction in 62 hr
  3. concentrationThe mixture was concentrated to 3.5 g black oil
  4. custompurified by flash chromatography (heptane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-8518ceaeebf644c89ccad75cf15a3f7f
Source dataset
uspto-grants-2012_01
Patent number
US08088955B2

Reaction notes

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