Allyl bromide → HCID 77754145, compound

HRID 727551Notes

Reaction equation

[CH:1]([N-]C(C)C)([CH3:3])[CH3:2].[Li+].[CH3:9][CH:10]([CH3:39])[CH2:11][CH:12]1[CH2:17][C@@H:16]([CH2:18][O:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:15][C:13]1=[O:14].C(Br)C=C>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH3:9][CH:10]([CH3:39])[CH2:11][C:12]1([C:1]([CH3:3])=[CH2:2])[CH2:17][CH:16]([CH2:18][O:19][C:20]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[O:15][C:13]1=[O:14]

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium diisopropylamide (8.3 mL, 16.6 mmol, 2.0M, heptane/THF/ethylbenzene) is added to a solution of (γS)-α-(2-methylpropyl)-γ-trityloxymethyl-γ-butyrolactone (5.67 g, 13.7 mmol), THF (50 mL), and HMPA (2.9 mL) at -78° C. After stirring for 30 minutes at -78° C., a solution of allyl bromide (1.46 mL, 16.9 mmol) and THF (8.0 mL) is added. The solution is allowed to stir for 4 hours at -78° C. and is then quenched with aqueous ammonium chloride (50 mL). After warming to room temperature, aqueous workup (EtOAc, MgSO4) and purification by flash chromatography (6:1 hexane:EtOAc) to give 5.12 g of the title compound (82%) as a white powder (mp 84°-85° C.).

Workup

stirringto stir for 4 hours at -78° C.
customis then quenched with aqueous ammonium chloride (50 mL)
temperatureAfter warming to room temperature
customaqueous workup (EtOAc, MgSO4) and purification by flash chromatography (6:1 hexane:EtOAc)

Sources & evidence

ORD record: ord-d86bc2ef4f86424083ab5f3b33e35d54
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

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