Diisobutylaluminumhydride → HCID 22491029, compound

HRID 2180613Notes

Reaction equation

C([O:3][C:4](=O)/[C:5](/[F:29])=[C:6](\[C:10]1[C:19]([O:20][CH2:21][CH3:22])=[C:18]([Br:23])[C:17]2[C:16]([CH3:25])([CH3:24])[CH2:15][CH:14]=[C:13]([CH:26]([CH3:28])[CH3:27])[C:12]=2[CH:11]=1)/[CH:7]([CH3:9])[CH3:8])C.[H-].C([Al+]CC(C)C)C(C)C>>[Br:23][C:18]1[C:17]2[C:16]([CH3:25])([CH3:24])[CH2:15][CH:14]=[C:13]([CH:26]([CH3:28])[CH3:27])[C:12]=2[CH:11]=[C:10](/[C:6](/[CH:7]([CH3:9])[CH3:8])=[C:5](/[F:29])\[CH2:4][OH:3])[C:19]=1[O:20][CH2:21][CH3:22]

Participants

Reactant 2

HCID 21225700Diisobutylaluminumhydride

HCID 69732052HCID 69732052, compound

Product 1

HCID 22491029HCID 22491029, compound

Procedure

Following General Procedure G-1, (2E)-3-(4-bromo-3-ethoxy-8-isopropyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-2-fluoro-4-methyl-pent-2-enoic acid ethyl ester (Compound A-127, 196 mg, 0.40 mmol) and diisobutylaluminum hydride (1 M in methylene chloride, 1.0 mL, 1.0 mmol) were reacted to give the title compound as a yellow syrup after purification by flash chromatography (silica gel, 10% ethyl acetate in hexanes).

Workup

customwere reacted

Sources & evidence

ORD record: ord-9f0ae2e9258945a89a6b505d81e4a9d3
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887896B1

Reaction notes

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