Tetrahydrofuran → (3R,4R,5S)-5-[(1R,2E)-3-(2-bromophenyl)-1-hydroxyprop-2-en-1-yl]-4-hydroxy-3-methoxydihydrofuran-2(3H)-one

HRID 1670439Notes

Reaction equation

HRID 1670439 reaction equation
[OH:1][C@@H:2]1[C@H:6]([C@H:7]([OH:10])[CH:8]=[CH2:9])[O:5][C:4](=[O:11])[C@@H:3]1[O:12][CH3:13].[Br:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1C=C.C1COCC1>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.C(Cl)Cl>[Br:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1/[CH:9]=[CH:8]/[C@H:7]([C@@H:6]1[O:5][C:4](=[O:11])[C@H:3]([O:12][CH3:13])[C@@H:2]1[OH:1])[OH:10]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 162642-BromostyreneHCID 67241097(3R,4R,5S)-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]-3-methoxydihydrofuran-2(3H)-one

Product 1

HCID 57617788(3R,4R,5S)-5-[(1R,2E)-3-(2-bromophenyl)-1-hydroxyprop-2-en-1-yl]-4-hydroxy-3-methoxydihydrofuran-2(3H)-oneYield 26%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

400 mg of 31 (2.13 mmol), 1.56 g of 2-bromostyrene (8.5 mmol), 1 mL of THF, 16 mL of CH2Cl2 and 54 mg of 2nd generation Grubb's catalyst (C46H65Cl2N2PRu, MW 848.98, 0.06 mmol) are added to a 100 mL round-bottomed flask. The medium is stirred for 24 h at RT. The solvent is evaporated, the crude product (1.9 g) is chromatographed on a silica cartridge (90 g), eluting with a CH2Cl2/MeOH (95/5) mixture. 190 mg of expected product 45 are obtained.

Workup

  1. customThe solvent is evaporated
  2. customthe crude product (1.9 g) is chromatographed on a silica cartridge (90 g)
  3. washeluting with a CH2Cl2/MeOH (95/5) mixture

Sources & evidence

ORD record
ord-f128da0054774267a34f7540ffdab577
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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