Hydrochloric Acid → HCID 54497740, compound

HRID 1459100Notes

Reaction equation

[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:5][CH:4]=1.[B:24](OC)([O:27]C)[O:25]C.Cl>C1COCC1.BrCCBr>[CH2:10]([O:9][C:6]1[CH:7]=[CH:8][C:3]([B:24]([OH:27])[OH:25])=[CH:4][CH:5]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: -78 °C

Procedure

Magnesium turnings (1.84 g, 0.08 mol) were added to a stirred solution, at room temperature under dry nitrogen, of compound 31 (15.00 g, 0.040 mol) in dry THF (150 ml) containing 1,2-dibromoethane (2 drops). The reaction mixture was maintained under these conditions for 1 h and then heated under reflux for 1 h. The reaction mixture was cooled to -78° C. and a solution of trimethyl borate (5.75 g, 0.08 mol) in dry THF (50 ml) was added dropwise. The reaction mixture was allowed to warm to room temperature overnight and then stirred for 1 h with 10% hydrochloric acid (100 ml). The product was extracted into ether (twice), and the combined ethereal extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo to yield a white solid.

Workup

temperatureThe reaction mixture was maintained under these conditions for 1 h
temperatureheated
temperatureunder reflux for 1 h
temperatureto warm to room temperature overnight
extractionThe product was extracted into ether (twice), and the combined ethereal extracts
washwere washed with water
dry with materialdried (MgSO4)
customThe solvent was removed in vacuo
customto yield a white solid

Sources & evidence

ORD record: ord-c878740bb14b445384c15b5b052be2f5
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05853613

Reaction notes

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