4-Morpholinobenzaldehyde → HCID 59138684, compound

HRID 1514076Notes

Reaction equation

HRID 1514076 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.O1CCN(C2C=CC(C=O)=CC=2)CC1.S1C=CC=C1[Mg]Br.[CH3:41][O:42][C:43]([O:47][Si](C)(C)C)=[C:44]([CH3:46])[CH3:45]>[Ti](Cl)(Cl)(Cl)Cl>[CH3:45][C:44]([CH3:46])([CH:13]([C:10]1[CH:11]=[CH:12][C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:8][CH:9]=1)[C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[C:43]([O:42][CH3:41])=[O:47]

Participants

6

Reactant 4

HCID 2913494-MorpholinobenzaldehydeHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 59138581(4-Morpholinophenyl)-(thiophen-2-yl)methanolHCID 178418438HCID 178418438, compound

Product 1

HCID 59138684HCID 59138684, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

In a similar manner to Preparation 1, Step 2, the reaction of (4-morpholinophenyl)-(thiophen-2-yl)methanol (675 mg, 2.45 mmol), prepared from 4-morpholinobenzaldehyde and thiophen-2-ylmagnesium bromide, and (1-methoxy-2-methylprop-1-enyloxy)trimethylsilane (2.48 ml, 12.3 mmol) in the presence of titanium tetrachloride (1M in DCM, 5.40 ml. 5.40 mmol) afforded methyl 2,2-dimethyl-3-(4-morpholinophenyl)-3-(thiophen-2-yl)propanoate (725 mg, 82.5% yield).). 1H NMR (400 MHz, CDCl3): δ 1.15 (s, 3H), 1.20 (s, 3H), 3.06 (m, 4H), 3.51 (s, 3H), 3.78 (m, 4H), 4.59 (s, 1H), 6.76 (d, 1H, J=8.5 Hz), 6.83 (m, 1H), 6.87 (m, 1H), 7.06 (m, 1H), 7.20 (d, 1H, J=8.5 Hz). HPLC Rt: 3.181 min.

Workup

  1. customIn a similar manner to Preparation 1, Step 2

Sources & evidence

ORD record
ord-ec558c881efd4d2a9e3d478e3ef43252
Source dataset
uspto-grants-2012_07
Patent number
US08222247B2

Reaction notes

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