Potassium Carbonate → HCID 66735822, compound

HRID 2405144Notes

Reaction equation

HRID 2405144 reaction equation
[Si:1]([O:8][C@H:9]([C@H:17]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])/[CH:18]=[CH:19]/I)[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[Br:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1/[CH:19]=[CH:18]/[C@@H:17]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2773294(2-Bromophenyl)boronic acidHCID 86600623HCID 86600623, compound

Product 1

HCID 66735822HCID 66735822, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

The product from Step 1 (64 mg, 0.127 mmol), was placed in a microwave tube together with commercially available 2-bromo phenyl boronic acid (27 mg, 0.129 mmol), potassium carbonate (51 mg, 0.372 mmol), Pd(PPh3)4 (7 mg, 5 mol %), and dioxane (1.5 mL). The tube was sealed, degassed, purged with argon, and heated to 60° C. The reaction mixture was stirred for 12 h, after which time it was quenched with saturated ammonium chloride, extracted with ether, dried, and concentrated. The product was purified by preparatory TLC (silica plate, 8% ethyl acetate/hexanes) to afford 50 mg (70%) of (5S,6R,E)-methyl 8-(2-bromophenyl)-5,6-bis(tert-butyldimethylsilyloxy)oct-7-enoate. 1H NMR (360 MHz, CDCl3): δ 7.49 (dd, J=20 Hz, 7.7 Hz, 2H), 7.24 (t, J=8.3 Hz, 1H), 7.06 (t, J=7.4 Hz, 1H), 6.84 (d, J=15.4 Hz, 1H), 6.10 (dd, J=15.9 Hz, 7.3 Hz), 4.48 (m, 1H), 3.63 (s, 3H), 2.29 (t, J=7.5 Hz), 1.71 (m, 2H), 1.53 (m, 2H), 0.894 (s, 9H), 0.857 (s, 9H), 0.084 (s, 3H), 0.080 (s, 6H), 0.016 (s, 3H). 13C NMR (500 MHz, CDCl3): δ 136.90, 136.61, 132.903, 129.93, 128.59, 127.42, 126.99, 77.0, 76.0, 50.9, 34.35, 33.04, 29.70, 25.99, 20.67, 10.17, −3.95, −4.76.

Workup

  1. customThe tube was sealed
  2. customdegassed
  3. custompurged with argon
  4. customafter which time it was quenched with saturated ammonium chloride
  5. extractionextracted with ether
  6. customdried
  7. concentrationconcentrated
  8. customThe product was purified by preparatory TLC (silica plate, 8% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-38c7f4ecb45f407e980667f88c416f8f
Source dataset
uspto-grants-2014_08
Patent number
US08802881B2

Reaction notes

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