2-Methyl-2-butene → 2-(4-Bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetic acid

HRID 514142Notes

Reaction equation

HRID 514142 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([CH:19]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH:20]=[O:21])[C:3]=1[CH3:30].CC(=CC)C.P([O-])(O)(O)=[O:37].[Na+].Cl([O-])=O.[Na+].OS([O-])(=O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[C:4]([CH:19]([O:22][Si:23]([C:26]([CH3:27])([CH3:29])[CH3:28])([CH3:24])[CH3:25])[C:20]([OH:37])=[O:21])[C:3]=1[CH3:30]

Participants

7

Reactant 5

HCID 105532-Methyl-2-buteneHCID 516919Sodium BisulfateHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866915662-(4-Bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetaldehyde

Product 1

HCID 671261952-(4-Bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyloxy)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A DCM solution (8.0 mL) of 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-(tert-butyldimethylsilyl-oxy)acetaldehyde (0.65 g, 1.29 mmol) was combined with 2-methyl-2-butene (1.5 mL, 14.1 mmol), sodium dihydrogen phosphate (8.0 mL, 1.0 M) and sodium chlorite (1.37 g, 14.46 mmol) and stirred vigorously overnight. The mixture was diluted 200% with DCM, the acidity adjusted to pH<5 with 2 M NaHSO4 and extracted with DCM (3×20 mL). The extracts were combined dried and concentrated under vacuo. The crude mixture was observed to contain the desired carboxylic acid (0.741 g) according to 1H NMR analysis and was used without purification. 1H-NMR: (400 MHz, CD3OD): δ 8.35 (d, J=8.4 Hz, 1H); 7.58-7.51 (m, 3H); 7.46-7.44 (m, 1H); 7.39-7.33 (m, 1H); 7.31-7.22 (m, 2H); 5.33 (s, 1H); 2.72 (s, 3H); 0.825 (s, 9H); −0.03 (s, 3H); −0.26 (s, 3H).

Workup

  1. extractionextracted with DCM (3×20 mL)
  2. customThe extracts were combined dried
  3. concentrationconcentrated under vacuo
  4. customwas used without purification

Sources & evidence

ORD record
ord-75aa18d60af2448f8695456d50952979
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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