Lithium Hexamethyldisilazide → HCID 86760277, compound

HRID 1244741Notes

Reaction equation

[CH2:1]([O:8][CH:9]([CH3:15])[CH:10]([B:12]([OH:14])[OH:13])[Cl:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]12([OH:27])[CH2:24][CH:20]([C:21]1([CH3:23])[CH3:22])[CH2:19][CH2:18][C:17]2([OH:26])[CH3:25].[Li+].C[Si]([N-:33][Si](C)(C)C)(C)C>C1COCC1>[CH2:1]([O:8][CH:9]([CH3:15])[CH:10]([B:12]([OH:14])[OH:13])[NH2:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]12([OH:27])[CH2:24][CH:20]([C:21]1([CH3:23])[CH3:22])[CH2:19][CH2:18][C:17]2([OH:26])[CH3:25].[ClH:11]

Participants

Conditions

Temperature: -78 °C

Procedure

Pinanediol (2-benzyloxy-1-chloropropyl)boronate, dissolved (3.85 g, 10.6 mmol)) in THF (60 mL), was added to a solution of LiHMDS (10.6 mmol) in THF at −78° C. The solution was stirred for 1 h at −78° C. and allowed to warm to room temperature. Solvent was evaporated and the residue redissolved in hexanes (120 mL). The solid was filtered and the filtrate recooled to −78° C., and a solution of HCl in 1,4-dioxane (4 N, 8.0 mL) was added. The solution was allowed to warm to room temperature while stirring overnight. The solvent was evaporated to yield 2.55 g (63%) of a brown oil. 1H-NMR (CDCl3) d 8.11 (br s, 3H), 7.35 (m, 5H), 4.57 (m, 2H), 4.32 (m, 1H), 3.16 (br s, 1H), 2.34-1.83 (m, 6H), 1.38 (s, 3H), 1.33 (m, 3H), 1.24 (s, 3H), 0.79 (s, 3H).

Workup

temperatureto warm to room temperature
customSolvent was evaporated
dissolutionthe residue redissolved in hexanes (120 mL)
filtrationThe solid was filtered
customrecooled to −78° C.
additiona solution of HCl in 1,4-dioxane (4 N, 8.0 mL) was added
temperatureto warm to room temperature
stirringwhile stirring overnight
customThe solvent was evaporated

Sources & evidence

ORD record: ord-a6749d161f9d429da6522dfe853db7ee
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122627B2

Reaction notes

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