Tert-butyl 3-hydroxypent-4-enoate → HCID 66747402, compound

HRID 931367Notes

Reaction equation

HRID 931367 reaction equation
[OH:1][CH:2]([CH:11]=[CH2:12])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(C(C(C)C)=C[CH2:18][B:19]([O-])[O-:20])(C)C>C(Cl)Cl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[OH:20][B:19]1[CH2:18][CH:12]=[CH:11][CH:2]([CH2:3][C:4]([O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:5])[O:1]1

Participants

5

Reactant 2

HCID 11769016Tert-butyl 3-hydroxypent-4-enoateHCID 86661960HCID 86661960, compound

Product 1

HCID 66747402HCID 66747402, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl 3-hydroxypent-4-enoate, XLVI (674 mg, 3.92 mmol) in DCM (15 mL) was added diisopropylallylboronate XLV (2 g, 11.76 mmol) via syringe. To the mixture was then added Grubbs' first generation catalyst (260 mg, 0.31 mmol, 7.5 mol %) and the vessel was purged with argon. The reaction was heated at 65° C. under nitrogen for 18 h. The mixture was concentrated under vacuum and the residue was purified by flash column chromatography (100% hexane→30% EtOAc/hexane) to afford tert-butyl 2-(2-hydroxy-3,6-dihydro-2H-1,2-oxaborinin-6-yl)acetate XLVII (770 mg, 3.63 mmol, 92.7% yield).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was purified by flash column chromatography (100% hexane→30% EtOAc/hexane)

Sources & evidence

ORD record
ord-57e34db757434bdb97c01a0ac52f4316
Source dataset
uspto-grants-2016_03
Patent number
US09296763B2

Reaction notes

Loading…